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[ CAS No. 120014-07-5 ] {[proInfo.proName]}

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Chemical Structure| 120014-07-5
Chemical Structure| 120014-07-5
Structure of 120014-07-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 120014-07-5 ]

CAS No. :120014-07-5 MDL No. :MFCD08693144
Formula : C24H27NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :LPMOTUSFDTTWJL-UDWIEESQSA-N
M.W : 377.48 Pubchem ID :10762160
Synonyms :

Calculated chemistry of [ 120014-07-5 ]

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.38
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 114.83
TPSA : 38.77 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.79
Log Po/w (XLOGP3) : 4.18
Log Po/w (WLOGP) : 3.75
Log Po/w (MLOGP) : 2.98
Log Po/w (SILICOS-IT) : 5.01
Consensus Log Po/w : 3.94

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.8
Solubility : 0.00597 mg/ml ; 0.0000158 mol/l
Class : Moderately soluble
Log S (Ali) : -4.7
Solubility : 0.00748 mg/ml ; 0.0000198 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.76
Solubility : 0.0000661 mg/ml ; 0.000000175 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.57

Safety of [ 120014-07-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 120014-07-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 120014-07-5 ]
  • Downstream synthetic route of [ 120014-07-5 ]

[ 120014-07-5 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 2107-69-9 ]
  • [ 22065-85-6 ]
  • [ 120014-07-5 ]
YieldReaction ConditionsOperation in experiment
100% With potassium hydroxide In water; toluene at 20℃; Inert atmosphere; Reflux Example 4; 5,6-Dimethoxyindan-1-one (60.0 g), 1-benzylpiperidine-4-carbaldehyde (70.5 g), potassium hydroxide (13.6 g) and benzyltriethylammonium chloride (3.56 g) were suspended in a mixture of toluene (380 mL) and water (42 mL) at room temperature. Nitrogen was bubbled through the suspension for 30 minutes, and the mixture was then heated to reflux temperature. After stirring at reflux temperature for 8 hours, water was added (380 mL), and the toluene was removed from the reaction mixture by distillation. The resulting crystals were isolated by filtration to yield 140 g of Compound 1. (Yield: Quantitative; Loss on Drying: 13.3percent, 121 g).
93.4% With sodium methylate In methanol; ethanol at 79℃; for 1.58333 h; Heating / reflux Example 8
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using ethanol and sodium methoxide and adopting method B
Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 30 mL of ethanol.
After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution with refluxing (79°C).
After completion of the pouring, stirring was continued with refluxing for 1 hour and 35 minutes to complete the reaction, whereby crystals were precipitated.
The crystals were precipitated during the refluxing.
Then, the reaction solution was cooled to 5°C (cooling rate: 32°C/hour).
The crystals precipitated at 5°C or higher were collected by filtration, washed with water (30 mL) and 6 mL of methanol and then dried at 50°C (drying time: 2 hours) to obtain 3.67 g of the crystals of the title compound (yield: 93.4percent).
1H-NMR data of these crystals agreed with those obtained in Example 1.
93.9% With sodium methylate In methanol at 66℃; for 1 h; Heating / reflux Example 3
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using methanol and sodium methoxide and adopting method B
Into a 100-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 30 mL of methanol.
After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution with refluxing (66°C).
After completion of the pouring, stirring was continued with refluxing for 1 hour to complete the reaction, whereby crystals were precipitated.
The crystals began to be precipitated (precipitation temperature: 66°C) 2 minutes after the pouring.
The reaction solution was cooled to 5°C (cooling rate: 26°C/hour) with ice water and the crystals precipitated at 5°C or higher were collected by filtration.
The crystals collected by filtration were washed with water (30 ml) and 6 mL of methanol and dried at 50°C (drying time: 1 hour and 30 minutes) to obtain 3.69 g of the crystals of the title compound (yield: 93.9percent).
1H-NMR data of these crystals agreed with those obtained in Example 1.
92.9% With sodium ethanolate In ethanol at 75 - 79℃; for 1.2 h; Heating / reflux Example 18
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using ethanol and sodium ethoxide and adopting method B
Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 30 mL of ethanol.
After the air in the system was replaced with nitrogen, a solution of 0.85 g (12.5 mmol, 1.2 equivalents) of sodium ethoxide in 4.5 mL of ethanol was poured into the reaction solution with refluxing (75°C).
After completion of the pouring, stirring was continued with refluxing (76-79°C) for 1 hour and 12 minutes to complete the reaction, whereby crystals were precipitated.
The crystals were precipitated during the refluxing.
Then, the reaction solution was cooled (cooling rate: 35°C/hour) and the crystals precipitated at 5°C or higher were collected by filtration.
The crystals collected by filtration were washed with water (30 mL) and 6 mL of methanol and dried at 50°C (drying time: 1 hour) to obtain 3.65 g of the crystals of the title compound (yield: 92.9percent).
1H-NMR data of these crystals agreed with those obtained in Example 1.
87.6% With sodium methylate In tetrahydrofuran; methanol at 17 - 43℃; for 1 h; Comparative Example 1
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine by the process described in Example 1 in patent document 3
Into a 100-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 30 mL of tetrahydrofuran.
After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was added dropwise at 17 to 23°C.
After completion of the dropwise addition, the resulting mixture was continuously stirred as it was for 1 hour.
After 40 mL of water was added to the reaction solution, the resulting mixture was cooled with ice water, and the crystals precipitated were collected by filtration.
The crystals collected by filtration were washed with water (50 mL) and methanol (3 mL x 2) and dried at 24-25°C for 13 hours and 40 minutes to obtain 3.46 g of the crystals of the title compound (yield: 88.10).
1H-NMR data of these crystals agreed with those obtained in Example 1.
Comparative Example 2 Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine by the process described in Example 2 in patent document 3 Into a 100-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 30 mL of tetrahydrofuran, and 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was added dropwise thereto at 37 to 43°C. After completion of the dropwise addition, the resulting mixture was continuously stirred as it was for 1 hour. After 40 mL of water was added to the reaction solution, the resulting mixture was cooled with ice water, and the crystals precipitated were collected by filtration. The crystals collected by filtration were washed with water (50 mL) and methanol (3 mL x 2) and dried at 24-25°C for 13 hours and 40 minutes to obtain 3.44 g of the crystals of the title compound (yield: 87.6percent). 1H-NMR data of these crystals agreed with those obtained in Example 1.
84.3% With sodium hydroxide In methanol; toluene at 65℃; for 1 h; Heating / reflux Example 20
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using a mixed solvent of methanol and toluene and sodium hydroxide and adopting method A
Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 24 mL of a mixed solvent (methanol: toluene = 16: 14).
After the air in the system was replaced with nitrogen, 0.5 g (12.5 mmol, 1.2 equivalents) of sodium hydroxide was added to the reaction solution with refluxing (65°C).
After completion of the addition, stirring was continued with refluxing for 1 hour to complete the reaction.
Then, the reaction solution was air-cooled until crystals were precipitated.
After the precipitation, the reaction solution was further cooled (cooling rate: 36°C/hour) and the crystals precipitated at 4°C or higher were collected by filtration.
The crystals began to be precipitated at 49°C.
The crystals collected by filtration were washed with water (30 mL) and 6 mL of methanol and dried at 50°C (drying time: 2 hours and 35 minutes) to obtain 3.31 g of the crystals of the title compound (yield: 84.3percent).
1H-NMR data of these crystals agreed with those obtained in Example 1.
84% With sodium hydroxide In methanol at 20℃; for 3 h; Inert atmosphere A solution of 5,6-dimethoxy-indanone (5, 19 g, 0.10 mol) in methanol (8 mL) is stirred under inert atmosphere at room temperature. Slowly add NaOH flakes (12.8 g, 0.32 mol) followed by N-benzyl-piperidine-4-carboxaldehyde (4, 20.2 g, 0.10 mol) to the reaction mixture. The mixture was stirred at room temperature for 3 h and progress of the reaction was monitored by TLC (hexane:ethyl acetate; 1:1). Once the reaction is complete, the solid formed was filtered, washed with 5 percent acetic acid and then with methanol and dried. The obtained solid (34 g) was taken into a round bottom flask and refluxed with DMF (50 mL). Gradually cooled to room temperature and stirred for 2 h, filtered the solid formed, wash with chilled methanol to afford a pale yellow crystalline solid 6 (32.0 g, 84 percent); m.p.: 175-177°C.
82.5% With sodium methylate In methanol; ethanol; toluene at 79℃; for 1 h; Heating / reflux Example 9
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using a mixed solvent of ethanol and toluene and sodium methoxide and adopting method A
Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 24 mL of a mixed solvent (ethanol: toluene = 16: 14).
After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution with refluxing (79°C).
After completion of the pouring, stirring was continued with refluxing for 1 hour to complete the reaction.
Then, the reaction solution was cooled to 3°C (cooling rate: 25°C/hour).
Crystals began to be precipitated at 46°C.
The crystals were collected by filtration, washed with water (30 mL) and 6 mL of methanol and then dried at 50°C (drying time: 2 hours) to obtain 3.24 g of the crystals of the title compound (yield: 82.5percent).
1H-NMR data of these crystals agreed with those obtained in Example 1.
79.9% With sodium methylate In methanol; propan-1-ol at 71 - 90℃; for 1 h; Heating / reflux Example 12
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using 1-propanol and sodium methoxide and adopting method B
Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 30 mL of 1-propanol.
After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution at an internal temperature of 71°C.
After completion of the pouring, stirring was continued with refluxing (about 90°C) for 1 hour to complete the reaction, whereby crystals were precipitated.
The crystals began to be precipitated before the refluxing.
Then, the reaction solution was cooled (cooling rate: 38°C/hour) and the crystals precipitated at 7°C or higher were collected by filtration.
The crystals collected by filtration were washed with water (30 mL) and 6 mL of methanol and dried at 50°C (drying time: 2 hours) to obtain 3.14 g of the crystals of the title compound (yield: 79.90).
1H-NMR data of these crystals agreed with those obtained in Example 1.
78.2% With sodium methylate In methanol; isopropyl alcohol at 60 - 80℃; for 1 h; Heating / reflux Example 10
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using 2-propanol and sodium methoxide and adopting method B
Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 30 mL of 2-propanol.
After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution at an internal temperature of 60°C.
After completion of the pouring, stirring was continued with refluxing (about 80°C) for 1 hour to complete the reaction, whereby crystals were precipitated.
The crystals began to be precipitated (precipitation temperature: 70°C) before the refluxing.
Then, the reaction solution was cooled (cooling rate: 33°C/hour) and the crystals precipitated at 7°C or higher were collected by filtration.
The crystals collected by filtration were washed with water (30 ml) and 6 mL of methanol and dried at 50°C (drying time: 2 hours) to obtain 3.07 g of the crystals of the title compound (yield: 78.20).
1H-NMR data of these crystals agreed with those obtained in Example 1.
76.4% With sodium methylate In tetrahydrofuran; methanol; toluene at 79℃; for 1 h; Heating / reflux Example 15
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using a mixed solvent of tetrahydrofuran and toluene and sodium methoxide and adopting method A
Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 24 mL of a mixed solvent (tetrahydrofuran: toluene = 16: 14).
After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution with refluxing (79°C).
After completion of the pouring, stirring was continued with refluxing for 1 hour to complete the reaction.
Then, the reaction solution was cooled (cooling rate: 30°C/hour) and the crystals precipitated at 4°C or higher were collected by filtration.
The crystals began to be precipitated at 44°C.
The crystals collected by filtration were washed with water (30 mL) and 6 mL of methanol and dried at 50°C (drying time: 2 hours and 25 minutes) to obtain 3.00 g of the crystals of the title compound (yield: 76.4percent).
1H-NMR data of these crystals agreed with those obtained in Example 1.
75.4% With sodium methylate In methanol; toluene at 23 - 64℃; for 1 - 4.51667 h; Example 1
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using a mixed solvent of methanol and toluene and sodium methoxide and adopting method A
Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 24 ml of a mixed solvent (methanol: toluene = 16: 14).
After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution at 64°C.
After completion of the pouring, stirring was continued with refluxing for 1 hour to complete the reaction.
Then, the reaction solution was air-cooled until crystals were precipitated (precipitation temperature: 45°C).
After the precipitation, the reaction solution was cooled (cooling rate: 18°C/hour) and the crystals precipitated at 5°C or higher were collected by filtration.
The crystals collected by filtration were washed with water (30 ml) and 6 mL of methanol and dried at 50°C (1 hour and 20 minutes) and then at 110°C (1 hour and 10 minutes) to obtain 3.53 g of the crystals of the title compound (yield: 89.9percent).
1H-NMR (400MHz,CDCl3) δ(ppm)=1.60-1.72(4H, m), 2.03-2.09(2H, m), 2.29-2.37(1H, m), 2.92-2.95(2H, m), 3.53 (2H, s), 3.60(2H, d, J=2Hz), 3.93 (3H, s), 3.98(3H, s), 6.67(1H, dt, J=10, 2Hz), 6.90(1H, s), 7.25-7.34(6H, m)
Example 2 Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine 1/2 toluene solvate using a mixed solvent of methanol and toluene and sodium methoxide and adopting method A The process of Example 1 was repeated except for conducting the drying of crystals at 50°C (1 hour and 20 minutes) only. 1 H-NMR (400MHz, CDCl3) 6 (ppm) =1 . 58-1.72 (4H, m), 2.03-2.09(2H, m), 2.28-2.38(2.5H, m), 2.91-2.94(2H, m), 3.53(2H, s), 3.59(2H, d, J=2Hz), 3.93(3H, s), 3.97(3H, s), 6.67(1H, dt, J=10, 2Hz), 6.90(1H, s), 7.13-7.33(8.5H, m) In TG-DTA (Thermogravimetry Differential Thermal Analysis) of the dried crystals, a weight loss corresponding to 1/2 toluene was recognized together with a heat absorption peak at about 100°C. In addition, these crystals and crystals obtained by further drying them at 110°C (1 hour and 10 minutes) showed different patterns, respectively, in powder X-ray diffraction.; Example 4 Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using a mixed solvent of methanol and toluene and sodium methoxide and adopting method A Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 24 ml of a mixed solvent (methanol: toluene = 16: 14). After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution at 61°C. After completion of the pouring, stirring was continued at 54-63°C for 1 hour to complete the reaction. Then, the reaction solution was air-cooled until crystals were precipitated (precipitation temperature: 50°C). After the precipitation of the crystals, the reaction solution was cooled (cooling rate: 25°C/hour) and the crystals precipitated at 6°C or higher were collected by filtration. The crystals collected by filtration were washed with water (30 ml) and 6 mL of methanol and dried at 50°C (drying time: 3 hours and 10 minutes) to obtain 3.24 g of the crystals of the title compound (yield: 82.5percent). 1H-NMR data of these crystals agreed with those obtained in Example 1.; Example 5 Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using a mixed solvent of methanol and toluene and sodium methoxide and adopting method B Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 24 mL of a mixed solvent (methanol : toluene = 16 : 14). After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution at 50°C. After the pouring, stirring was continued at 45-53°C for 1 hour to complete the reaction, whereby crystals were precipitated. The crystals began to be precipitated (precipitation temperature: 48°C) 47 minutes after the pouring. After the continuous stirring at 45-53°C for 1 hour, the reaction solution was cooled (cooling rate: 22°C/hour) and the crystals precipitated at 3°C or higher were collected by filtration. The crystals collected by filtration were washed with water (30 mL) and 6 mL of methanol and dried at 50°C (drying time: 3 hours and 10 minutes) to obtain 3.17 g of the crystals of the title compound (yield: 80.70). 1H-NMR data of these crystals agreed with those obtained in Example 1; Example 6 Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using a mixed solvent of methanol and toluene and sodium methoxide and adopting method B Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 24 ml of a mixed solvent (methanol : toluene = 16 : 14). After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution at 28°C. After completion of the pouring, stirring was continued at 23-30°C for 4 hours and 31 minutes to complete the reaction, whereby crystals were precipitated. The crystals began to be precipitated (precipitation temperature: 26°C) 1 hour after the pouring. After the continuous stirring at 23-30°C for 4 hours and 31 minutes, the reaction solution was ice-cooled (cooling rate: 18°C/hour) and the crystals precipitated at 7°C or higher were collected by filtration. The crystals collected by filtration were washed with water (30 ml) and 6 mL of methanol and dried at 50°C (drying time: 1 hour and 23 minutes) to obtain 2.96 g of the crystals of the title compound (yield: 75.4percent). 1H-NMR data of these crystals agreed with those obtained in Example 1.
75.9% With sodium methylate In methanol; ethyl acetate at 65 - 71℃; for 1.08333 h; Heating / reflux Example 19
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using ethyl acetate and sodium methoxide and adopting method B
Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 30 mL of ethyl acetate.
After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution at 65°C.
After completion of the pouring, stirring was continued with refluxing (about 71°C) for 1 hour and 5 minutes to complete the reaction.
Crystals were precipitated during the refluxing.
Then, the reaction solution was cooled (cooling rate: 31°C/hour) and the crystals precipitated at 5°C or higher were collected by filtration.
The crystals collected by filtration were washed with water (30 mL) and 6 mL of methanol and dried at 50°C (drying time: 1 hour) to obtain 2.98 g of the crystals of the title compound (yield: 75.9percent).
1H-NMR data of these crystals agreed with those obtained in Example 1.
73.1% With sodium methylate In methanol; isopropyl alcohol; toluene at 83℃; for 1.03333 h; Heating / reflux Example 11
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using a mixed solvent of 2-propanol and toluene and sodium methoxide and adopting method A
Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 24 mL of a mixed solvent (2-propanol: toluene = 16: 14).
After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution with refluxing (83°C).
After completion of the pouring, stirring was continued with refluxing for 1 hour and 2 minutes to complete the reaction.
Then, the reaction solution was cooled to 7°C (cooling rate: 33°C/hour).
Crystals began to be precipitated at 42°C.
The crystals were collected by filtration, washed with water (30 ml) and 6 mL of methanol and then dried at 50°C (drying time: 1 hour and 20 minutes) to obtain 2.87 g of the crystals of the title compound (yield: 73.1percent).
1H-NMR data of these crystals agreed with those obtained in Example 1.
72.6% With sodium methylate In methanol; toluene at 60 - 85℃; for 1 h; Heating / reflux Example 14 Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using toluene and sodium methoxide and adopting method A Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 30 mL of toluene. After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution at 66°C. After completion of the pouring, stirring was continued with refluxing (85°C) for 1 hour to complete the reaction. Then, the reaction solution was cooled (cooling rate: 31°C/hour) and the crystals precipitated at 5°C or higher were collected by filtration. The crystals began to be precipitated at 37°C. The crystals collected by filtration were washed with water (30 mL) and 6 mL of methanol and dried at 50°C (drying time: 2 hours and 25 minutes) to obtain 2.85 g of the crystals of the title compound (yield: 72.60). 1H-NMR data of these crystals agreed with those obtained in Example 1.; Example 16
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using a mixed solvent of methanol and toluene and sodium methoxide and adopting method A
Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 24 mL of a mixed solvent (methanol: toluene = 12: 18).
After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution at 60°C.
After completion of the pouring, stirring was continued with refluxing (67°C) for 1 hour to complete the reaction.
Then, the reaction solution was cooled (cooling rate: 26°C/hour) and the crystals precipitated at 5°C or higher were collected by filtration.
The crystals began to be precipitated at 42°C.
The crystals collected by filtration were washed with water (30 mL) and 6 mL of methanol and dried at 50°C (1 hour and 20 minutes) and then at 110°C (1 hour and 5 minutes) to obtain 3.49 g of the crystals of the title compound (yield: 88.9percent).
1H-NMR data of these crystals agreed with those obtained in Example 1.
Example 17 Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using a mixed solvent of methanol and toluene and sodium methoxide and adopting method A Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 24 mL of a mixed solvent (methanol : toluene = 6 : 24). After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution at 62°C. After completion of the pouring, stirring was continued with refluxing (about 71°C) for 1 hour to complete the reaction. Then, the reaction solution was cooled (cooling rate: 29°C/hour) and the crystals precipitated at 7°C or higher were collected by filtration. The crystals began to be precipitated at 60°C. The crystals collected by filtration were washed with water (30 mL) and 6 mL of methanol and dried at 50°C (1 hour and 20 minutes) and then at 100°C (1 hour and 5 minutes) to obtain 3.44 g of the crystals of the title compound (yield: 87.6percent). 1H-NMR data of these crystals agreed with those obtained in Example 1.
70% With sodium hydroxide In methanol at 20 - 66℃; for 6 h; Preparation of l-Benzyl-4-[5,6-dimethoxy-l-indanon)-2-ylidenyIlinethyl piperidine. Sodium hydroxide (1.46g) was added to methanol (150ml) followed by addition of 5,6-dimethoxy-l-indanone (5g) and l-benzylρiρeridene-4-carboxaldehyde (6.8g) at 20-30°C.The temperature of the reaction mass was gradually raised to 62-660C and was stirred for 6 hours. The reaction mass was concentrated under vacuum and 2/3 volume of the reaction mass was recovered. The remaining slurry was filtered and the product was washed with water followed by methanol to give 6.9 g of l-benzyl-4-[5,6-dimethoxy-l-indanon)-2-ylidenyl] methyl piperidine (yield=70percent), having purity 98.5percent by HPLC.
69.3% With sodium methylate In tetrahydrofuran; methanol at 63℃; for 1 h; Heating / reflux Example 7
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using tetrahydrofuran and sodium methoxide and adopting method A
Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 30 mL of tetrahydrofuran.
After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution with refluxing (63°C).
After completion of the pouring, stirring was continued with refluxing for 1 hour to complete the reaction.
Then, the reaction solution was cooled to 4°C (cooling rate: 30°C/hour).
Crystals began to be precipitated at 28°C.
The crystals precipitated at 4°C or higher were collected by filtration, washed with water (30 ml) and 6 mL of methanol and then dried at 50°C (drying time: 2 hours and 40 minutes) to obtain 2.72 g of the crystals of the title compound (yield: 69.3percent).
1H-NMR data of these crystals agreed with those obtained in Example 1.
63.9% With sodium methylate In methanol; propan-1-ol; toluene at 95℃; for 1 h; Heating / reflux Example 13
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using a mixed solvent of 1-propanol and toluene and sodium methoxide and adopting method A
Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 24 mL of a mixed solvent (1-propanol: toluene = 16: 14).
After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution with refluxing (95°C).
After completion of the pouring, stirring was continued with refluxing for 1 hour to complete the reaction.
Then, the reaction solution was cooled to 5°C (cooling rate: 38°C/hour).
Crystals began to be precipitated at 40°C.
The crystals were collected by filtration, washed with water (30 mL) and 6 mL of methanol and then dried at 50°C (drying time: 2 hours and 40 minutes) to obtain 2.51 g of the crystals of the title compound (yield: 63.9percent).
1H-NMR data of these crystals agreed with those obtained in Example 1.
62.9% With sodium methylate In methanol; 1,2-dimethoxyethane at 60 - 80℃; for 1 h; Heating / reflux Example 21
Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using 1,2-dimethoxyethane and sodium methoxide and adopting method A
Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 30 mL of 1,2-dimethoxyethane.
After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution at 63°C.
After completion of the pouring, stirring was continued with refluxing (80°C) for 1 hour to complete the reaction.
Then, the reaction solution was cooled (cooling rate: 52°C/hour) and the crystals precipitated at 5°C or higher were collected by filtration.
The crystals began to be precipitated at 48°C.
The crystals collected by filtration were washed with water (30 mL) and 6 mL of methanol and dried at 50°C (drying time: 2 hours and 35 minutes) to obtain 2.47 g of the crystals of the title compound (yield: 62.90).
1H-NMR data of these crystals agreed with those obtained in Example 1.
Example 22 Production of 1-benzyl-4-[(5,6-dimethoxy-1-indanon)-2-ylidene]methylpiperidine using a mixed solvent of methanol and 1,2-dimethoxyethane and sodium methoxide and adopting method B Into a 50-mL four-necked flask were charged 2.0 g (10.4 mmol) of 5,6-dimethoxy-1-indanone, 2.5 g (12.3 mmol, 1.2 equivalents) of 1-benzyl-4-formylpiperidine and 24 mL of a mixed solvent (methanol: 1,2-dimethoxyethane = 16 : 14). After the air in the system was replaced with nitrogen, 2.4 g (12.4 mmol, 1.2 equivalents) of a 28percent-sodium methoxide/methanol solution was poured into the reaction solution at 60°C. After completion of the pouring, stirring was continued with refluxing (about 68°C) for 1 hour to complete the reaction, whereby crystals were precipitated. The crystals were precipitated during the refluxing. Then, the reaction solution was cooled (cooling rate: 26°C/hour) and the crystals precipitated at 8°C or higher were collected by filtration. The crystals collected by filtration were washed with water (30 mL) and 6 mL of methanol and dried at 50°C (1 hour and 20 minutes) and then at 110°C (1 hour and 30 minutes) to obtain 3.67 g of the crystals of the title compound (yield: 93.40). 1H-NMR data of these crystals agreed with those obtained in Example 1.
60% With sodium methylate In methanol at 20 - 65℃; for 2 h; Preparation of Benzyl-4-f(5, 6-dimethoxy-1-indanon)-2-ylidenyl]methylpiperidine. A solution 9.8 g of sodium methoxide in 60 ml of methanol was added to a stirred solution of 25 g of 5,6-dimethoxy-l-indanone and 36.75 g 1-benzyl piperidene-4- carboxaldehyde in methanol (690ml) at 20-3 O0C. The temperature of the reaction mass was gradually raised to 60-650C and stirred for 2 hours. The precipitated solid was filtered and the product was washed with water followed by methanol to give crude product which was converted to its hydrochloride salt using methanol. The hydrochloride salt was basified using sodium hydroxide to obtain 26.9 g of 1-benzyl-4- [5, 6-dimethoxy-l-indanon)-2-ylidenyl] methyl piperidine (yield=60percent) having purity 99.92percent by HPLC.

Reference: [1] Patent: US2009/253746, 2009, A1, . Location in patent: Page/Page column 3
[2] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 11-12
[3] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 10
[4] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 14
[5] Organic Process Research and Development, 2008, vol. 12, # 4, p. 731 - 735
[6] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 15-16
[7] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 14-15
[8] Asian Journal of Chemistry, 2017, vol. 29, # 9, p. 1999 - 2004
[9] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 12
[10] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 12-13
[11] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 12
[12] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 13
[13] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 10-11
[14] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 14
[15] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 12
[16] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 13-14
[17] Patent: WO2007/108011, 2007, A2, . Location in patent: Page/Page column 12-13
[18] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 11
[19] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 13
[20] Patent: EP1911745, 2008, A1, . Location in patent: Page/Page column 15
[21] Patent: WO2007/108011, 2007, A2, . Location in patent: Page/Page column 13
[22] Journal of Medicinal Chemistry, 1995, vol. 38, # 24, p. 4821 - 4829
[23] Patent: US2006/172992, 2006, A1, . Location in patent: Page/Page column 1.b
[24] Patent: US2007/191610, 2007, A1, . Location in patent: Page/Page column 3
[25] Patent: WO2008/10235, 2008, A2, . Location in patent: Page/Page column 17
[26] Patent: US2010/143505, 2010, A1, . Location in patent: Page/Page column 15
[27] Patent: US2006/135507, 2006, A1, . Location in patent: Page/Page column 18
[28] Patent: EP1779867, 2007, A1, . Location in patent: Page/Page column 31-32
[29] Patent: WO2011/51957, 2011, A2, . Location in patent: Page/Page column 9-10
  • 2
  • [ 22065-85-6 ]
  • [ 4693-38-3 ]
  • [ 120014-07-5 ]
YieldReaction ConditionsOperation in experiment
89% at 55 - 175℃; for 11 h; Inert atmosphere Under nitrogen, in the three-necked flask were successively added 3-chloro-1- (3,4-dimethoxyphenyl) propan-1-one () 22.9g (0.10mol), N- benzyl-4 - piperidinyl carbaldehyde () 22.4g (0.11mol), [Et3NH] Cl-AlCl3(2: 3, according to AlCl3Counted 0.3mol), to control the temperature of 55 ~ 60 and maintained 5 hours, heated to 165 ~ 175 and maintained for 6 hours, TLC monitoring of the reaction end, after the completion of the reaction, cooled to room temperature, and the ionic liquid is automatically layered product , product layer was poured into 5percent hydrochloric acid and ice water, suction filtration to give the crude product, recrystallized from ethyl acetate to give 1-benzyl-4- (5,6-dimethoxy-2-methyl-1-indanone ) - piperidine () 33.6g, yield 89percent, purity 99.7percent, in addition to the ionic liquid layer was recycled water.
Reference: [1] Patent: CN105418488, 2016, A, . Location in patent: Paragraph 0039; 0042; 0043
  • 3
  • [ 22065-85-6 ]
  • [ 120014-07-5 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: With sodium methylate In tetrahydrofuran at 60℃; for 0.5 - 0.75 h;
Stage #2: at 5 - 30℃; for 3.5 h;
Example-4; Preparation of 1 -Benzyl -4- [(5, 6 dimethoxy-l-indanonV2-ylidenylmethyl piperidineTo a solution of l .Og of 5, 6 dimethoxy indanone dissolved in 25ml THF, 0.562 g of sodium methoxide was added. The reaction contents were heated to 6O0C and maintained for 30 min before cooling to 1O0C. A solution of 1.Ig of N-benzyl 4-formyl piperidine dissolved in 25ml THF was then added drop-wise over a period of 30 min keeping the temperature less than 1O0C. After complete addition, the reaction was slowly warmed to 25-3O0C and stirred for 3h. The reaction mass was quenched in cold water and extracted with 100ml of ethyl acetate. The organic layer was washed with 2 X 100ml water and 100ml of sodium chloride solution and dried over anhydrous sodium sulphate. The organic layer was concentrated under vacuum to obtain an off- white solid (IAg, 71percent yield).; Step-d; - 1 -Benzyl -4- IY5, 6 dmethoxy-l-indanon)-2^ ylidenylmethyl piped dine 78.5g of 5,6 dimetlioxy indanone was dissolved in 500ml of THF and 66g of sodium methoxide added to it. The mixture was heated to 6O0C and kept for 30-45min before cooling to 50C. 88.5g of step-d product was dissolved in 500ml of THF and added drop-wise over a period of 30 min with temperature maintained .5-1O0C. Once the addition was over, the reaction mixture, was wanned to room temperature and stirred for 3h. The reaction mass was poured into cold water and extracted into 2.5L of ethyl acetate, washed with water and then with brine The organic layer was dried with sodium sulphate and concentrated to obtain a solid (109g)
Reference: [1] Patent: WO2007/77443, 2007, A1, . Location in patent: Page/Page column 8; 10
  • 4
  • [ 1126-09-6 ]
  • [ 120014-07-5 ]
Reference: [1] Organic Process Research and Development, 2008, vol. 12, # 4, p. 731 - 735
[2] Asian Journal of Chemistry, 2017, vol. 29, # 9, p. 1999 - 2004
  • 5
  • [ 100-44-7 ]
  • [ 120014-07-5 ]
Reference: [1] Organic Process Research and Development, 2008, vol. 12, # 4, p. 731 - 735
[2] Asian Journal of Chemistry, 2017, vol. 29, # 9, p. 1999 - 2004
  • 6
  • [ 24228-40-8 ]
  • [ 120014-07-5 ]
Reference: [1] Organic Process Research and Development, 2008, vol. 12, # 4, p. 731 - 735
[2] Asian Journal of Chemistry, 2017, vol. 29, # 9, p. 1999 - 2004
  • 7
  • [ 67686-01-5 ]
  • [ 120014-07-5 ]
Reference: [1] Organic Process Research and Development, 2008, vol. 12, # 4, p. 731 - 735
[2] Asian Journal of Chemistry, 2017, vol. 29, # 9, p. 1999 - 2004
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