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[ CAS No. 280774-04-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 280774-04-1
Chemical Structure| 280774-04-1
Chemical Structure| 280774-04-1
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Product Details of [ 280774-04-1 ]

CAS No. :280774-04-1 MDL No. :MFCD09971191
Formula : C9H17NO Boiling Point : -
Linear Structure Formula :- InChI Key :NQCIDPPGMMMYBU-UHFFFAOYSA-N
M.W : 155.24 Pubchem ID :17893923
Synonyms :

Calculated chemistry of [ 280774-04-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.89
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.27
TPSA : 20.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.98
Log Po/w (XLOGP3) : 1.02
Log Po/w (WLOGP) : 0.92
Log Po/w (MLOGP) : 1.07
Log Po/w (SILICOS-IT) : 1.56
Consensus Log Po/w : 1.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.31
Solubility : 7.55 mg/ml ; 0.0486 mol/l
Class : Very soluble
Log S (Ali) : -1.04
Solubility : 14.3 mg/ml ; 0.092 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.13
Solubility : 11.5 mg/ml ; 0.074 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.08

Safety of [ 280774-04-1 ]

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 [ 280774-04-1 ]

* 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.

  • Downstream synthetic route of [ 280774-04-1 ]

[ 280774-04-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 280774-03-0 ]
  • [ 280774-04-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at 0℃; for 0.166667h; Stage #2: (1-Isopropyl-piperidin-4-yl)-methanol In dichloromethane at 0℃; for 2.25h; Stage #3: With triethylamine In dichloromethane for 0.166667h; 134.2 Reference Example 134: 3-(1-Isopropylpiperidin-4-yl)acrylic acid hydrochloride (1) Lithium aluminum hydride (1.10 g) is suspended in tetrahydrofuran (80 ml), and thereto is added a solution of ethyl 1-isopropylpiperidine-4-carboxylate (5.00 g) obtained in Reference Example 127 in tetrahydrofuran (30 ml) dropwise under ice-cooling. The reaction solution is stirred for 2 hours under the ice-cooling, and water (1.1 ml), 15 % aqueous sodium hydroxide solution (1.1 ml) and water (3.3 ml) are added dropwise successively and stirred for additional 10 minutes. To the resulting reaction solution is added potassium carbonate, and the mixture is stirred for 20 minutes, and then the insoluble materials are removed by filtration. The filtrate is concentrated under reduced pressure, and then the resulting residue is purified by NH-silica gel column chromatography (eluent: chloroform/ethyl acetate = 1/1) to give (1-isopropylpiperidin-4-yl)methanol (4.29 g). APCI-MS M/Z:158[M+H]+.(2) Oxalyl chloride (2.0 ml) is dissolved in dichloromethane (120 ml) and thereto is added dropwise a solution of dimethylsulfoxide (3.3 ml) in dichloromethane (15 ml) under dry ice-acetone cooling. After stirring for 10 minutes under ice-cooling, a solution of (1-isopropylpiperidin-4-yl)methanol (3.00 g) obtained in Reference Example 134(1) in dichloromethane (30 ml) is added dropwise over a period of 15 minutes. After addition, the reaction solution is stirred for 2 hours under ice-cooling, and thereto is added dropwise triethylamine (13.3 ml) over a period of 10 minutes. The reaction solution is stirred for one hour while it is warmed to room temperature, and then the solution is poured to saturated aqueous sodium hydrogen carbonate solution. The mixture is extracted with dichloromethane and evaporated to remove the solvent under reduced pressure. The aqueous layer is extracted with ethyl acetate, and the extract is combined with the residue obtained by removing solvent from the above dichloromethane-extract, washed with water and saturated brine and dried over sodium sulfate. The solvent is evaporated under reduced pressure to give the crude material, 1-isopropylpiperidine-4-carbaldehyde (1.96 g). APCI-MS M/Z:156[M+H]+.(3) Triethyl phosphonoacetate (7.96 g) is dissolved in tetrahydrofuran (50 ml) and thereto is added gradually 60 % sodium hydride in oil (1.45 g) under ice-cooling. After stirring for 20 minutes under ice-cooling, to the mixture is added 1-isopropylpiperidine-4-carbaldehyde (5.03 g) obtained in Reference Example 134(2) in tetrahydrofuran (25 ml). The reaction solution is stirred for 3 hours, diluted with diethyl ether, thereto is added water and the mixture is extracted with ethyl acetate. The organic layer is washed with water and saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate = 9/1) to give ethyl 3-(1-isopropylpiperidin-4-yl)acrylate (6.87 g). APCI-MS M/Z:226[M+H]+.(4) Ethyl 3-(1-isopropylpiperidin-4-yl)acrylate (1.01 g) obtained in Reference Example 134(3) is dissolved in ethanol (20 ml), thereto is added 2 N aqueous sodium hydroxide solution (4.5 ml) and the mixture is stirred at room temperature for 24 hours. To the reaction solution is added 2 N hydrochloric acid (9 ml), and the mixture is concentrated under reduced pressure, and then the resulting residue is lyophilized to give the title compound (1.43 g). APCI-MS M/Z:198[M+H]+.
  • 2
  • [ 280774-04-1 ]
  • ethyl 3-(1-isopropylpiperidin-4-yl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: 1-Isopropylpiperidine-4-carboxaldehyde In tetrahydrofuran for 3h; 134.3 Reference Example 134: 3-(1-Isopropylpiperidin-4-yl)acrylic acid hydrochloride (1) Lithium aluminum hydride (1.10 g) is suspended in tetrahydrofuran (80 ml), and thereto is added a solution of ethyl 1-isopropylpiperidine-4-carboxylate (5.00 g) obtained in Reference Example 127 in tetrahydrofuran (30 ml) dropwise under ice-cooling. The reaction solution is stirred for 2 hours under the ice-cooling, and water (1.1 ml), 15 % aqueous sodium hydroxide solution (1.1 ml) and water (3.3 ml) are added dropwise successively and stirred for additional 10 minutes. To the resulting reaction solution is added potassium carbonate, and the mixture is stirred for 20 minutes, and then the insoluble materials are removed by filtration. The filtrate is concentrated under reduced pressure, and then the resulting residue is purified by NH-silica gel column chromatography (eluent: chloroform/ethyl acetate = 1/1) to give (1-isopropylpiperidin-4-yl)methanol (4.29 g). APCI-MS M/Z:158[M+H]+.(2) Oxalyl chloride (2.0 ml) is dissolved in dichloromethane (120 ml) and thereto is added dropwise a solution of dimethylsulfoxide (3.3 ml) in dichloromethane (15 ml) under dry ice-acetone cooling. After stirring for 10 minutes under ice-cooling, a solution of (1-isopropylpiperidin-4-yl)methanol (3.00 g) obtained in Reference Example 134(1) in dichloromethane (30 ml) is added dropwise over a period of 15 minutes. After addition, the reaction solution is stirred for 2 hours under ice-cooling, and thereto is added dropwise triethylamine (13.3 ml) over a period of 10 minutes. The reaction solution is stirred for one hour while it is warmed to room temperature, and then the solution is poured to saturated aqueous sodium hydrogen carbonate solution. The mixture is extracted with dichloromethane and evaporated to remove the solvent under reduced pressure. The aqueous layer is extracted with ethyl acetate, and the extract is combined with the residue obtained by removing solvent from the above dichloromethane-extract, washed with water and saturated brine and dried over sodium sulfate. The solvent is evaporated under reduced pressure to give the crude material, 1-isopropylpiperidine-4-carbaldehyde (1.96 g). APCI-MS M/Z:156[M+H]+.(3) Triethyl phosphonoacetate (7.96 g) is dissolved in tetrahydrofuran (50 ml) and thereto is added gradually 60 % sodium hydride in oil (1.45 g) under ice-cooling. After stirring for 20 minutes under ice-cooling, to the mixture is added 1-isopropylpiperidine-4-carbaldehyde (5.03 g) obtained in Reference Example 134(2) in tetrahydrofuran (25 ml). The reaction solution is stirred for 3 hours, diluted with diethyl ether, thereto is added water and the mixture is extracted with ethyl acetate. The organic layer is washed with water and saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate = 9/1) to give ethyl 3-(1-isopropylpiperidin-4-yl)acrylate (6.87 g). APCI-MS M/Z:226[M+H]+.(4) Ethyl 3-(1-isopropylpiperidin-4-yl)acrylate (1.01 g) obtained in Reference Example 134(3) is dissolved in ethanol (20 ml), thereto is added 2 N aqueous sodium hydroxide solution (4.5 ml) and the mixture is stirred at room temperature for 24 hours. To the reaction solution is added 2 N hydrochloric acid (9 ml), and the mixture is concentrated under reduced pressure, and then the resulting residue is lyophilized to give the title compound (1.43 g). APCI-MS M/Z:198[M+H]+.
  • 3
  • [ 473720-85-3 ]
  • [ 280774-04-1 ]
  • (R)-3-(4-ethoxy-phenyI)-2-{1-[(1-isopropyl-piperidin-4-ylmethyl)-amino]-ethyl}-3H-quinazolin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at -45 - 20℃; for 0.583333h; 1 To a solution of 18.7g l-isopropyl-piperidine-4-carbaldehyde (0.12 mol, 1.00 equiv.) dissolved in 300 mL 1,2-dichloroethane cooled to -45°C internal temperature was added 37.3g Al (0.12 mol, 1.00 equiv.) in three equivalentportions at 5 min. intervals. The mixture was stirred at -45° C for 15 min. then 39g sodiumtriacetoxyborohydride (0.18 mol, 1.50 equiv.) was added in three equivalent portions at 5min. intervals. The reaction mixture was allowed to equilibrate slowly from -45° C to roomtemperature overnight. Saturated aqueous sodium bicarbonate solution was added untilaqueous layer pH=9-10. The separated aqueous layer was extracted twice withdichloromethane. The combined organic layers were dried over magnesium sulfate, filteredand concentrated in vacua to afford A2 as a glassy solid, which was used without furtherpurification. 1HNMR(400MHz; CDC13; T=298.1 K) 5 1.01 (d, 3=6.6 Hz, 6H), 1.11-1.29(m, 2H), 1.23 (d, J=6.6 Hz, 3H), 1.11-1.41 (m, 1H), 1.46 (t, J=6.9 Hz, 3H), 1.72 (dd, J=14.2,33.2 Hz, 2H), 1.98-2.20 (m, 3H), 2.20-2.37 (m, 2H), 2.58-2.73 (m, 1H), 2.78-2.92 (m, 2H),3.43 (dd, J=7.6, 7.6 Hz, 1H), 4.10 (qt, J=6.9 Hz, 2H), 6.97-7.08 (m, 2H), 7.08-7.18 (m, 2H),7.46 (dd, J=8.5, 8.5 Hz, 1H), 7.69 (d, J=8.5 Hz, 1H), 8.27 (d, J=8.5 Hz, 1H) ppm.
  • 4
  • [ 114615-82-6 ]
  • [ 280774-03-0 ]
  • [ 280774-04-1 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine In dichloromethane 272.D D. D. 1-Isopropylpiperidine-4-carboxaldehyde A solution of 1-isopropylpiperidine-4-methanol (0.40 g, 2.5 mmol) and N-methylmorpholine (0.46 g, 3.8 mmol) in methylene chloride (20 mL) was treated with tetrapropylammonium perruthenate (0.089 g, 0.25 mmol). After 3 h, the mixture was concentrated and the residue purified by column chromatography (SiO2: 10% to 20% methanol:methylene chloride) affording 0.20 g (50%) of the title compound. 1NMR; FIA-MS, m/e 156 (m+).
  • 5
  • [ 79-37-8 ]
  • [ 280774-03-0 ]
  • [ 280774-04-1 ]
YieldReaction ConditionsOperation in experiment
With sodium bicarbonate; dimethyl sulfoxide; triethylamine In dichloromethane; water; ethyl acetate R.2 Reference Example 2 Reference Example 2 Oxalyl chloride (3.15 ml) was dissolved in 30 ml of dichloromethane, a solution of 3.20 ml of dimethyl sulfoxide in 6 ml of dichloromethane was added thereto at-70ØC, the mixture was stirred for 15 minutes, a solution of 2.93 g of (1-isopropyl-4-piperidyl)methanol in 15 ml of dichloromethane was added thereto at -70ØC and the mixture was stirred for 1 hour. After 12.5 ml of triethylamine were added at -70ØC, the mixture was raised to room temperature, then water and a saturated aqueous solution of sodium hydrogen carbonate were added and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated in vacuo and ethyl acetate was added to the resulting residue. After removing the insoluble matter by filtration, the solvent was evaporated in vacuo to give 1.15 g of 1-isopropylpiperidine-4-carbaldehyde. This compound was used for the next reaction without purification.
  • 6
  • [ 280774-04-1 ]
  • [ 365462-81-3 ]
  • N-(5-chloro-pyridin-2-yl)-3-hydroxy-2-[(1-isopropyl-4-piperidyl)methyl]amino}benzamide [ No CAS ]
  • N-(5-chloro-pyridin-2-yl)-3-hydroxy-2-[(1-isopropyl-4-piperidyl)methyl]amino}benzamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium bicarbonate; p-toluenesulfonic acid monohydrate; acetic acid In water; toluene 9 Example 9 Example 9 2-Amino-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide (100 mg) and 80 mg of 1-isopropylpiperidine-4-carbaldehyde were suspended in 5 ml of toluene, then 10 mg of p-toluenesulfonic acid hydrate were added thereto and the mixture was heated to reflux for 2 hours together with removal of water by an azeotropic operation. After the solvent was evaporated in vacuo, 7 ml of acetic acid and 88 mg of a boran-trimethylamine complex were added to the resulting residue and the mixture was stirred at 70ØC for 15 hours. The solvent was evaporatedin vacuo, a saturated aqueous solution of sodium hydrogen carbonate was added to the residue and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated in vacuo and the resulting residue was purified by means of a silica gel column chromatography. After addition of 1N hydrochloric acid and water to the resulting N-(5-chloro-2-pyridyl)-3-hydroxy-2-[(1-isopropyl-4-piperidyl)methyl]amino}benzamide and the mixture was freeze-dried to give 102 mg of N-(5-chloro-2-pyridyl)-3-hydroxy-2-[(1-isopropyl-4-piperidyl)methyl]amino}benzamide hydrochloride.
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