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Chemical Structure| 5778-62-1
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Product Details of [ 5778-62-1 ]

CAS No. :5778-62-1 MDL No. :MFCD11849269
Formula : C14H14ClN Boiling Point : -
Linear Structure Formula :- InChI Key :WTHWSNJNZUUKBX-UHFFFAOYSA-N
M.W : 231.72 Pubchem ID :10799552
Synonyms :

Safety of [ 5778-62-1 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5778-62-1 ]

* 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 [ 5778-62-1 ]

[ 5778-62-1 ] Synthesis Path-Downstream   1~20

YieldReaction ConditionsOperation in experiment
Rk.mit NaOMe (Kinetik): Geschw.-konst.; ΔS(excit.); ΔF(excit.); E(a);
YieldReaction ConditionsOperation in experiment
Acridon I (Y = 7-CH3, Z = OH), POCl3;
  • 3
  • [ 5778-62-1 ]
  • [ 111-68-2 ]
  • heptyl-(7-methyl-1,2,3,4-tetrahydro-acridin-9-yl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With phenol at 125 - 130℃; for 4h;
  • 6
  • [ 5778-62-1 ]
  • [ 100-46-9 ]
  • benzyl-(7-methyl-1,2,3,4-tetrahydro-acridin-9-yl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With phenol at 125 - 130℃; for 4h;
  • 7
  • [ 5778-62-1 ]
  • [ 141-43-5 ]
  • 2-((7-methyl-1,2,3,4-tetrahydroacridin-9-yl)amino)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In pentan-1-ol at 137℃; for 24h;
With potassium iodide; phenol at 180℃; for 6h; 6.1.5. Synthesis of 2-(7-methyl-1,2,3,4-tetrahydroacridin-9-yl)amino)ethan-1-ol (35) A mixture of 9-chloro-7-methyl-1,2,3,4-tetrahydroacridine (22,0.005 mol, 1.16 g), ethanolamine (0.05 mol, 3 ml), KI (0.01 mol,1.49 g), and phenol (0.025 mol, 2.35 g) was refluxed for about 6 h at180 C, then stirred overnight at room temperature. Then the reactionmixture was quenched using 30 ml NaOH solution (1 mol/l).The formed precipitate was filtered, washed several times withbrine solution, and dried. The dried solid was extracted with DCM,evaporated and washed with petroleum ether, and recrystallizedfrom methanol to afford compound 35. Light brown solid (1.16 g,91%). Mp 146e149 C. IR (KBr) v (cm1): 3347, 3160, 2932, 2852.1HNMR (CDCl3) d 7.86 (d, J 8.6 Hz, 1H, ArH), 7.76 (s, 1H, ArH), 7.40 (d,J 8.6 Hz, 1H, ArH), 4.65 (s, 1H, NH), 3.86 (t, J 5.0 Hz, 2H, CH2O),3.61 (brs, 2H, CH2N), 3.05 (t, J 5.7 Hz, 2H, CH2 of THA), 2.76 (2H, t,J 5.7 Hz, CH2 of THA), 2.51 (s, 4H, CH3 and OH), 1.91e1.88 (m, 4H,2CH2 of THA). 13C NMR (100 MHz, CDCl3) d 157.3, 150.4, 145.2, 133.7,130.8, 127.8, 121.6, 120.4, 117.2 (Ar), 62.0 (CH2O), 50.9 (CH2N), 33.5(CH2 of THA), 24.7 (CH2 of THA), 23.0 (CH2 of THA), 22.7 (CH2 ofTHA), 21.9 (AreCH3). MS m/z (%) for C16H20N2O: 256.33 (57.20,M),77.17 (100.00).
With potassium iodide; phenol at 180℃; for 6h; 6.1.5. Synthesis of 2-(7-methyl-1,2,3,4-tetrahydroacridin-9-yl)amino)ethan-1-ol (35) A mixture of 9-chloro-7-methyl-1,2,3,4-tetrahydroacridine (22,0.005 mol, 1.16 g), ethanolamine (0.05 mol, 3 ml), KI (0.01 mol,1.49 g), and phenol (0.025 mol, 2.35 g) was refluxed for about 6 h at180 C, then stirred overnight at room temperature. Then the reactionmixture was quenched using 30 ml NaOH solution (1 mol/l).The formed precipitate was filtered, washed several times withbrine solution, and dried. The dried solid was extracted with DCM,evaporated and washed with petroleum ether, and recrystallizedfrom methanol to afford compound 35. Light brown solid (1.16 g,91%). Mp 146e149 C. IR (KBr) v (cm1): 3347, 3160, 2932, 2852.1HNMR (CDCl3) d 7.86 (d, J 8.6 Hz, 1H, ArH), 7.76 (s, 1H, ArH), 7.40 (d,J 8.6 Hz, 1H, ArH), 4.65 (s, 1H, NH), 3.86 (t, J 5.0 Hz, 2H, CH2O),3.61 (brs, 2H, CH2N), 3.05 (t, J 5.7 Hz, 2H, CH2 of THA), 2.76 (2H, t,J 5.7 Hz, CH2 of THA), 2.51 (s, 4H, CH3 and OH), 1.91e1.88 (m, 4H,2CH2 of THA). 13C NMR (100 MHz, CDCl3) d 157.3, 150.4, 145.2, 133.7,130.8, 127.8, 121.6, 120.4, 117.2 (Ar), 62.0 (CH2O), 50.9 (CH2N), 33.5(CH2 of THA), 24.7 (CH2 of THA), 23.0 (CH2 of THA), 22.7 (CH2 ofTHA), 21.9 (AreCH3). MS m/z (%) for C16H20N2O: 256.33 (57.20,M),77.17 (100.00).
  • 8
  • [ 18595-16-9 ]
  • [ 5778-62-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / water / 20 °C 2: trichlorophosphate / neat (no solvent) / 115 °C
  • 9
  • [ 5778-62-1 ]
  • 3-methyl-2-(2-((7-methyl-1,2,3,4-tetrahydroacridin-9-yl)amino)ethoxy)-6-(pyridin-4-yl)pyrimidine-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: pentan-1-ol / 24 h / 137 °C 2.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C 2.2: 1 h / 20 °C
  • 10
  • [ 5778-62-1 ]
  • 3-methyl-2-((2-((7-methyl-1,2,3,4-tetrahydroacridin-9-yl)amino)ethyl)amino)-6-(pyridine-4-yl)pyrimidin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium iodide / pentan-1-ol / 137 °C 2: potassium carbonate / tetrahydrofuran / 66 °C
  • 12
  • [ 5778-62-1 ]
  • N-(2-chloroethyl)-7-methyl-1,2,3,4-tetrahydroacridin-9-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium iodide; phenol / 6 h / 180 °C 2: thionyl chloride / dichloromethane / 2 h
  • 13
  • [ 5778-62-1 ]
  • 7-methyl-N-(2-morpholinoethyl)-1,2,3,4-tetrahydroacridin-9-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium iodide; phenol / 6 h / 180 °C 2: thionyl chloride / dichloromethane / 2 h 3: triethylamine / acetone / 24 h / Reflux
  • 14
  • [ 5778-62-1 ]
  • 7-methyl-N-(2-(piperidin-1-yl)ethyl)-1,2,3,4-tetrahydroacridin-9-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium iodide; phenol / 6 h / 180 °C 2: thionyl chloride / dichloromethane / 2 h 3: triethylamine / acetone / 24 h / Reflux
  • 15
  • [ 5778-62-1 ]
  • 7-methyl-N-(2-(4-methylpiperazin-1-yl)ethyl)-1,2,3,4-tetrahydroacridin-9-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium iodide; phenol / 6 h / 180 °C 2: thionyl chloride / dichloromethane / 2 h 3: triethylamine / acetone / 24 h / Reflux
  • 16
  • [ 5778-62-1 ]
  • 1,4-bis(7-methyl-1,2,3,4-tetrahydroacridin-9-yl)piperazine [ No CAS ]
  • N-(2-(4-benzylpiperazin-1-yl)ethyl)-7-methyl-1,2,3,4-tetrahydroacridin-9-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium iodide; phenol / 6 h / 180 °C 2: thionyl chloride / dichloromethane / 2 h 3: potassium carbonate / ethanol / 12 h / Reflux
  • 17
  • [ 110-91-8 ]
  • [ 5778-62-1 ]
  • 4-(7-methyl-1,2,3,4-tetrahydroacridin-9-yl)morpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With potassium iodide; phenol at 60 - 180℃; for 6.5h; 6.1.3. General procedure for the synthesis of 9-substituted-7-methyl-1,2,3,4-tetrahydroacridin (25e31) General procedure: mixture of 9-chloro-7-substituted (or 6,7-disubstituted) 1,2,3,4-tetrahydroacridine (22, 23 or 24,0.0017 mol), secondary amine (morpholine, piperidine, or methylpiperazine)(0.0085 mol), KI (0.0034 mol, 0.51 g), and phenol(0.0068 mol, 0.64 g) was heated at 60 C for half an hour, thenrefluxed for about 6 h at 180 C, the reaction was monitored usingTLC. After the reaction completion the reaction mixture wasquenched using 30 ml of NaOH solution (1 mol/l). The formedprecipitate was filtered, washed several times with brine solutionand dried. The dried solid was extracted with DCM, evaporated andwashed with petroleum ether, and recrystallized from methanol toafford compounds 25, 26, 28 and 30, purified using preparative TLCusing elution system of (ethyl acetate/pet. ether) (8:2) to producecompounds 27 and 31 or purified with column chromatographyusing DCM to afford compound 29.6.1.3.1. 4-(7-Methyl-1,2,3,4-tetrahydroacridin-9-yl)morpholine (25).Yellow crystals. Yield: (0.2 g, 41%). Mp 181 C. 1H NMR (CDCl3) d 7.93(s, 1H, ArH), 7.88 (d, J 8.6 Hz, 1H, ArH), 7.44 (dd, J 8.6, 1.6 Hz, 1H,ArH), 3.95 (t, J 4.3 Hz, 4H, 2CH2 of morpholine), 3.34 (t, J 4.3 Hz,4H, 2CH2 of morpholine), 3.13 (t, J 6.4 Hz, 2H, CH2 of THA), 2.97 (t,J 6.4 Hz, 2H, CH2 of THA), 2.55 (s, 3H, CH3), 1.99e1.93 (m, 2H, CH2of THA), 1.91e1.85 (m, 2H, CH2 of THA). 13C NMR (100 MHz, CDCl3)d 159.2, 152.0, 146.1, 134.9, 130.8, 128.4, 127.8, 125.8, 122.6 (Ar), 68.0(2CH2 of morpholine), 50.7 (2CH2 of morpholine), 33.8 (CH2 ofTHA), 26.8 (CH2 of THA), 23.0 (CH2 of THA), 22.8 (CH2 of THA), 22.1(Ar-CH3). MS m/z (%) for C18H22N2O: 282.25 (100.00, M).
41% With potassium iodide; phenol at 60 - 180℃; for 6.5h; 6.1.3. General procedure for the synthesis of 9-substituted-7-methyl-1,2,3,4-tetrahydroacridin (25e31) General procedure: mixture of 9-chloro-7-substituted (or 6,7-disubstituted) 1,2,3,4-tetrahydroacridine (22, 23 or 24,0.0017 mol), secondary amine (morpholine, piperidine, or methylpiperazine)(0.0085 mol), KI (0.0034 mol, 0.51 g), and phenol(0.0068 mol, 0.64 g) was heated at 60 C for half an hour, thenrefluxed for about 6 h at 180 C, the reaction was monitored usingTLC. After the reaction completion the reaction mixture wasquenched using 30 ml of NaOH solution (1 mol/l). The formedprecipitate was filtered, washed several times with brine solutionand dried. The dried solid was extracted with DCM, evaporated andwashed with petroleum ether, and recrystallized from methanol toafford compounds 25, 26, 28 and 30, purified using preparative TLCusing elution system of (ethyl acetate/pet. ether) (8:2) to producecompounds 27 and 31 or purified with column chromatographyusing DCM to afford compound 29.6.1.3.1. 4-(7-Methyl-1,2,3,4-tetrahydroacridin-9-yl)morpholine (25).Yellow crystals. Yield: (0.2 g, 41%). Mp 181 C. 1H NMR (CDCl3) d 7.93(s, 1H, ArH), 7.88 (d, J 8.6 Hz, 1H, ArH), 7.44 (dd, J 8.6, 1.6 Hz, 1H,ArH), 3.95 (t, J 4.3 Hz, 4H, 2CH2 of morpholine), 3.34 (t, J 4.3 Hz,4H, 2CH2 of morpholine), 3.13 (t, J 6.4 Hz, 2H, CH2 of THA), 2.97 (t,J 6.4 Hz, 2H, CH2 of THA), 2.55 (s, 3H, CH3), 1.99e1.93 (m, 2H, CH2of THA), 1.91e1.85 (m, 2H, CH2 of THA). 13C NMR (100 MHz, CDCl3)d 159.2, 152.0, 146.1, 134.9, 130.8, 128.4, 127.8, 125.8, 122.6 (Ar), 68.0(2CH2 of morpholine), 50.7 (2CH2 of morpholine), 33.8 (CH2 ofTHA), 26.8 (CH2 of THA), 23.0 (CH2 of THA), 22.8 (CH2 of THA), 22.1(Ar-CH3). MS m/z (%) for C18H22N2O: 282.25 (100.00, M).
  • 18
  • [ 110-89-4 ]
  • [ 5778-62-1 ]
  • 7-methyl-9-(piperidin-1-yl)-1,2,3,4-tetrahydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With potassium iodide; phenol at 60 - 180℃; for 6.5h; 6.1.3. General procedure for the synthesis of 9-substituted-7-methyl-1,2,3,4-tetrahydroacridin (25e31) General procedure: mixture of 9-chloro-7-substituted (or 6,7-disubstituted) 1,2,3,4-tetrahydroacridine (22, 23 or 24,0.0017 mol), secondary amine (morpholine, piperidine, or methylpiperazine)(0.0085 mol), KI (0.0034 mol, 0.51 g), and phenol(0.0068 mol, 0.64 g) was heated at 60 C for half an hour, thenrefluxed for about 6 h at 180 C, the reaction was monitored usingTLC. After the reaction completion the reaction mixture wasquenched using 30 ml of NaOH solution (1 mol/l). The formedprecipitate was filtered, washed several times with brine solutionand dried. The dried solid was extracted with DCM, evaporated andwashed with petroleum ether, and recrystallized from methanol toafford compounds 25, 26, 28 and 30, purified using preparative TLCusing elution system of (ethyl acetate/pet. ether) (8:2) to producecompounds 27 and 31 or purified with column chromatographyusing DCM to afford compound 29.
  • 19
  • [ 109-01-3 ]
  • [ 5778-62-1 ]
  • 7-methyl-9-(4-methylpiperazin-1-yl )-1,2,3,4-tetrahydroacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With potassium iodide; phenol at 60 - 180℃; for 6.5h; 6.1.3. General procedure for the synthesis of 9-substituted-7-methyl-1,2,3,4-tetrahydroacridin (25e31) General procedure: mixture of 9-chloro-7-substituted (or 6,7-disubstituted) 1,2,3,4-tetrahydroacridine (22, 23 or 24,0.0017 mol), secondary amine (morpholine, piperidine, or methylpiperazine)(0.0085 mol), KI (0.0034 mol, 0.51 g), and phenol(0.0068 mol, 0.64 g) was heated at 60 C for half an hour, thenrefluxed for about 6 h at 180 C, the reaction was monitored usingTLC. After the reaction completion the reaction mixture wasquenched using 30 ml of NaOH solution (1 mol/l). The formedprecipitate was filtered, washed several times with brine solutionand dried. The dried solid was extracted with DCM, evaporated andwashed with petroleum ether, and recrystallized from methanol toafford compounds 25, 26, 28 and 30, purified using preparative TLCusing elution system of (ethyl acetate/pet. ether) (8:2) to producecompounds 27 and 31 or purified with column chromatographyusing DCM to afford compound 29.
  • 20
  • [ 5778-62-1 ]
  • [ 6752-16-5 ]
  • C20H19N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With potassium iodide; phenol at 180℃; for 6h; 6.1.4. Synthesis of 7-methyl-N-(1H-pyrazolo[3,4-b]pyridin-3-yl)-1,2,3,4-tetrahydroacridin-9-amine (32) A mixture of 9-chloro-7-methyl-1,2,3,4-tetrahydroacridine (22,0.0017 mol, 0.4 g), 1H-pyrazolo [3,4-b]pyridin-3-amine (7,0.0017 mol, 0.228 g), KI (0.0034 mol, 0.51 g), and phenol(0.0068 mol, 0.64 g)was heated under reflux at 180 C for about 6 h.The reaction mixture was quenched using 30 ml aqueous NaOHsolution (1 mol/l). The formed precipitate was filtered, washedseveral times with brine solution, extracted with ethyl acetate, andfinally purified with column chromatography using DCM, thenDCM/methanol (7:3) to afford compound 32. Light brown crystals.Yield: (0.3 g, 53%). Mp 170e172 C. 1H NMR (DMSO) d 12.43 (s, 1H,pyrazole NH), 8.75 (s,1H, NH), 8.47 (dd, J 4.4,1.4 Hz, 1H, ArH), 8.20(dd, J 8.0, 1.4 Hz, 1H, ArH), 7.82 (s, 1H, ArH), 7.78 (d, J 8.6 Hz, 1H,ArH), 7.46 (dd, J 8.6, 1.6 Hz, 1H, ArH), 7.10 (dd, J 8.0, 4.4 Hz, 1H,ArH), 3.02 (t, J 6.4 Hz, 2H, CH2 of THA), 2.61 (t, J 6.4 Hz, 2H, CH2of THA), 2.41 (s, 3H, CH3), 1.88e1.82 (m, 2H, CH2 of THA), 1.73e1.67(2H, m, CH2 of THA). 13C NMR (100 MHz, DMSO) d 158.7, 152.6,149.6, 145.7, 145.4, 143.4, 134.3, 131.0, 130.3, 128.5, 124.0, 123.6,122.5, 115.5, 107.0 (Ar), 33.8 (CH2 of THA), 25.9 (CH2 of THA), 23.0(CH2 of THA), 22.7 (CH2 of THA), 21.9 (Ar-CH3). MS m/z (%) forC20H19N5: 329.34 (25.97, M), 78.21 (100.00).
53% With potassium iodide; phenol at 180℃; for 6h; 6.1.4. Synthesis of 7-methyl-N-(1H-pyrazolo[3,4-b]pyridin-3-yl)-1,2,3,4-tetrahydroacridin-9-amine (32) A mixture of 9-chloro-7-methyl-1,2,3,4-tetrahydroacridine (22,0.0017 mol, 0.4 g), 1H-pyrazolo [3,4-b]pyridin-3-amine (7,0.0017 mol, 0.228 g), KI (0.0034 mol, 0.51 g), and phenol(0.0068 mol, 0.64 g)was heated under reflux at 180 C for about 6 h.The reaction mixture was quenched using 30 ml aqueous NaOHsolution (1 mol/l). The formed precipitate was filtered, washedseveral times with brine solution, extracted with ethyl acetate, andfinally purified with column chromatography using DCM, thenDCM/methanol (7:3) to afford compound 32. Light brown crystals.Yield: (0.3 g, 53%). Mp 170e172 C. 1H NMR (DMSO) d 12.43 (s, 1H,pyrazole NH), 8.75 (s,1H, NH), 8.47 (dd, J 4.4,1.4 Hz, 1H, ArH), 8.20(dd, J 8.0, 1.4 Hz, 1H, ArH), 7.82 (s, 1H, ArH), 7.78 (d, J 8.6 Hz, 1H,ArH), 7.46 (dd, J 8.6, 1.6 Hz, 1H, ArH), 7.10 (dd, J 8.0, 4.4 Hz, 1H,ArH), 3.02 (t, J 6.4 Hz, 2H, CH2 of THA), 2.61 (t, J 6.4 Hz, 2H, CH2of THA), 2.41 (s, 3H, CH3), 1.88e1.82 (m, 2H, CH2 of THA), 1.73e1.67(2H, m, CH2 of THA). 13C NMR (100 MHz, DMSO) d 158.7, 152.6,149.6, 145.7, 145.4, 143.4, 134.3, 131.0, 130.3, 128.5, 124.0, 123.6,122.5, 115.5, 107.0 (Ar), 33.8 (CH2 of THA), 25.9 (CH2 of THA), 23.0(CH2 of THA), 22.7 (CH2 of THA), 21.9 (Ar-CH3). MS m/z (%) forC20H19N5: 329.34 (25.97, M), 78.21 (100.00).
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