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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 : |
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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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Rk.mit NaOMe (Kinetik): Geschw.-konst.; ΔS(excit.); ΔF(excit.); E(a); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Acridon I (Y = 7-CH3, Z = OH), POCl3; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With phenol at 125 - 130℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With ammonia; phenol at 125 - 130℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With trichlorophosphate for 2h; Heating; | |
With trichlorophosphate In neat (no solvent) at 115℃; | ||
With trichlorophosphate at 110℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With phenol at 125 - 130℃; for 4h; |
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / water / 20 °C 2: trichlorophosphate / neat (no solvent) / 115 °C |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium iodide / pentan-1-ol / 137 °C 2: potassium carbonate / tetrahydrofuran / 66 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium iodide In pentan-1-ol at 137℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium iodide; phenol / 6 h / 180 °C 2: thionyl chloride / dichloromethane / 2 h |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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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