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CAS No. : | 878025-42-4 | MDL No. : | MFCD20528188 |
Formula : | C10H14N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 162.23 | Pubchem ID : | - |
Synonyms : |
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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: |
* 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 |
---|---|---|
85% | With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; 1,1-dichloroethane; at 20℃; for 15h; | To a solution of 6,7-dihydro-8(5H)-quinolinone included in general processes above (1.5 g, 10 mmol) in dichloroethane (50 mL) was added methyl amine (2 M in tetrahydrofuran, 10 mL, 20 mmol), acetic acid (580 mul_, 10 mmol), and sodium triacetoxyborohydride (4.3 g, 20 mmol). The mixture was stirred at room temperature for 15 hours and then filtered through a silica plug and rinsed with 10% ammonium hydroxide-acetonitrile. The solvent was removed and the residue purified by flash chromatography (0-10% ammonium hydroxide-acetonitrile) to give 1.4 g (85% yield) N-methyl-5,6,7,8-tetrahydro-8-quinolinamine as a yellow oil. 1H-NMR (CDCI3): delta 8.37 (d, 1 H), 7.36 (d, 1 H), 7.05 (t, 1H), 3.64 (t, 1 H), 2.75 (m, 2H), 2.52 (s, 3H), 2.11 (m, 1H), 1.96 (m, 1H), 1.75 (m, 2H); MS m/z 163 (M+1). |
85% | With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; 1,2-dichloro-ethane; at 20℃; for 15h; | To a solution of 6,7-dihydro-8(5H)-quinolinone included in general processes above (1.5 g, 10 mmol) in dichloroethane (50 ml_) was added methyl amine (2 M in tetrahydrofuran, 10 mL, 20 mmol), acetic acid (580 mul_, 10 mmol), and sodium triacetoxyborohydride (4.3 g, 20 mmol). The mixture was stirred at room temperature for 15 hours and then filtered through a silica plug and rinsed with 10% ammonium hydroxide-acetonitrile. The solvent was removed and the residue purified by flash chromatography (0-10% ammonium hydroxide-acetonitrile) to give 1.4 g (85% yield) Lambda/-methyl-5,6,7,8-tetrahydro-8-quinolinamine as a yellow oil. 1H-NMR (CDCI3): delta 8.37 (d, 1H), 7.36 (d, 1H), 7.05 (t, 1H), 3.64 (t, 1 H), 2.75 (m, 2H), 2.52 (s, 3H), 2.11 (m, 1H), 1.96 (m, 1H), 1.75 (m, 2H); MS m/z 163 (M+1 ). |
85% | With sodium tris(acetoxy)borohydride; acetic acid; In ethanol; 1,2-dichloro-ethane; at 20℃; for 24h; | Dissolve 6,7-dihydroquinolin-8(5H)-one (735 mg, 5 mmol) in 10 mL of 1,2-dichloroethane, A solution of methylamine in ethanol (1.45 mL, 10 mmol) was added successively. Acetic acid HOAc (290 muL, 5 mmol) and sodium triacetoxyborohydride (2.12 g, 10 mmol). The resulting mixture was stirred at room temperature for 24 h. Add saturated sodium bicarbonate solution to adjust the pH to 10, The layers were separated, and the aqueous phase was extracted three times with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was separated by column chromatography to give the title compound as a yellow oil. (688mg, yield 85%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium tris(acetoxy)borohydride; acetic acid; In 1,1-dichloroethane; at 20℃; for 15h; | To a solution of Lambda/-methyl-5,6,7,8-tetrahydro-8-quinolinamine (500 mg, 3.1 mmol) and 5-bromoimidazo[1 ,2-a]pyridine-2-carbaldehyde (770 mg, 3.4 mmol) in dichloroethane (17 ml_) was added acetic acid (180 mul_, 3.1 mmol) and sodium triacetoxyborohydride (2.0 g, 9.3 mmol). The mixture was stirred at room temperature for 15 hours and then filtered through a silica plug and rinsed with 10% ammonium hydroxide- acetonitrile. The solvent was removed and the residue diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate, and dried with magnesium sulfate to give 1.1 g (99% yield) of Lambda/-[(5-bromoimidazo[1 ,2-a]pyridin-2-yl)methyl]-Lambda/- methyl-5,6,7,8-tetrahydro-8-quinolinamine as an orange oil. 1H-NMR (CDCI3): delta 8.50 (d, 1H), 7.92 (s, 1 H), 7.49 (d, 1 H), 7.32 (d, 1 H), 7.03 (m, 2H), 6.96 (m, 1H), 4.09 (m, 1 H), 3.94 (s, 2H), 2.72 (m, 2H), 2.40 (s, 3H), 2.12 (m, 1H), 1.99 (m, 2H), 1.68 (m, 1H); MS m/z 372 (M+1). |
99% | With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃; for 15h; | To a solution of Lambda/-methyI-5,6,7,8-tetrahydro-8-quinolinamine (500 mg, 3.1 mmol) and 5-bromoimidazo[1 ,2-a]pyridine-2-carbaldehyde (770 mg, 3.4 mmol) in dichloroethane (17 mL) was added acetic acid (180 muL, 3.1 mmol) and sodium triacetoxyborohydride (2.0 g, 9.3 mmol). The mixture was stirred at room temperature for 15 hours and then filtered through a silica plug and rinsed with 10% ammonium hydroxide- acetonitrile. The solvent was removed and the residue diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate, and dried with magnesium sulfate to give 1.1 g (99% yield) of /V-[(5-bromoimidazo[1 ,2-a]pyridin-2-yl)methyl]-/V- methyl-5,6,7,8-tetrahydro-8-quinolinamine as an orange oil. 1H-NMR (CDCI3): delta 8.50 (d, 1H), 7.92 (S, 1H), 7.49 (d, 1 H), 7.32 (d, 1H), 7.03 (m, 2H), 6.96 (m, 1H), 4.09 (m, 1H), 3.94 (s, 2H), 2.72 (m, 2H), 2.40 (s, 3H), 2.12 (m, 1H), 1.99 (m, 2H), 1.68 (m, 1H); MS m/z 372 (M+1 ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | Stage #1: (±)-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine; kumujian C In methanol at 65℃; for 18h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; | 3 Example 3: Preparation of 7V-((9H-pyrido[3,4-b]indol-l-yl)methyl)-iV-methyl-5,6,7,8- tetrahydroquinolin-8-amine tetrahydrochloride (V).A solution of β-carboline-1-carbaldehyde, 2, (0.10 g, 0.50 mmol) in methanol (10 mL) was treated with N-methyl-5,6,7,8-tetrahydroquinolin-8-amine, 5, (0.09 g, 0.56 mmol). The resulting mixture was warmed to 65 0C and stirred for 18 h. The reaction mixture was then cooled to 0 0C and sodium borohydride (0.08 g, 2.03 mmol) was added portionwise. The reaction mixture was slowly warmed to room temperature and stirred for 1 h. A saturated aqueous solution of sodium bicarbonate was added. The product was extracted with dichloromethane. The combined organic layers were dried over potassium carbonate, filtered and concentrated in vacuo. The product was purified by silica gel chromatography (0-5 % methanol/CH2Cl2) to afford 0.07 g (40 % yield) of the desired product V: 1H NMR (400 MHz, CDCl3) 513.20 (bs, IH), 8.73 (d, J = 4.4 Hz, IH), 8.27 (d, J = 5.6 Hz, IH), 8.12 (d, J = 7.6 Hz, IH), 7.85 (d, J = 5.2 Hz, IH), 7.70 (d, J = 8.4 Hz, IH), 7.55 (t, J = 7.6 Hz, IH), 7.44 (d, J = 8.0 Hz, IH), 7.25-7.15 (m, 2H), 4.26-4.18 (m, 3H), 2.94-2.72 (m, 2H), 2.34-2.18 (m, IH), 2.24 (s, 3H), 2.15-2.05 (m, IH), 2.04-1.90 (m, IH), 1.85-1.70 (m, IH); ESI+ MS: m/z (rel intensity) 343.1 (90, [M+H]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | General procedure: A mixture of corresponding aldehyde (1.1 eq.), 31 (1.0 eq.), AcOH (1.0 eq.) in 1,2-dichloroethane (10mL) was stirred at 0C for 10min. NaBH(OAc)3 (1.5 eq.) was then added to the reaction solution at 0C. The resulting suspension was stirred at room temperature overnight. The reaction solution was diluted with water (10mL) and extracted with dichloromethane (30mL×3). The combined organic layers was dried over Na2SO4, filtered and evaporated. The residue was purified by silica gel column chromatography (dichloromethane/methanol=100/1) to give the desired product. 6.1.17.1 N-((2-Chloropyridin-4-yl)methyl)-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine (35b) Compound 35b was obtained as a yellow oil (yield 91%). 1H NMR (400?MHz, CDCl3) delta 8.50 (s, 1H), 8.25 (d, J?=?4.0?Hz, 1H), 7.39-7.35 (m, 2H), 7.27 (s, 1H), 7.07 (s, 1H), 3.95 (s, 1H), 3.73-3.58 (m, 2H), 2.79-2.69 (m, 2H), 2.30 (s, 3H), 2.06 (s, 2H), 1.92-1.89 (m, 1H), 1.70 (s, 1H). |