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CAS No. : | 1454-53-1 | MDL No. : | MFCD00012800 |
Formula : | C15H20ClNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YPFMNHZRNXPYBG-UHFFFAOYSA-N |
M.W : | 297.78 | Pubchem ID : | 102623 |
Synonyms : |
|
Chemical Name : | Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
61.4% | 6-Benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one A mixture of ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride (50.0 g, 0.168 mol), formamidine acetate (16.2 g, 0.201 mol), 4.37 M of sodium methoxide in methanol (190 mL) and methanol (200 mL, 5 mol) was heated to 85 C. for 16 hour in a 350 ml sealed reaction vessel. The mixture was allowed to cool and reduced in vacuo. The residue was dissolved in 1N NaOH (150 ml) and poured over ice. Glacial acetic acid was added to the mixture until the pH of the mixture was 7 and a tan solid precipitated out. the solid was filtered, washed with water and cold ether, and dried on high vacuum to yield the title compound as a tan solid. (26.2 g, 61.4%). MS: M+H=242.2. 1H NMR (DMSO-d6): delta 2.29 (t, 5.8 Hz, 2H); 2.61 (t, 5.8 Hz, 2H); 3.26 (s, 2H); 3.64 (s, 2H); 7.21-7.36 (m, 6H); 7.96 (s, 1H). | |
61.4% | Intermediate 16-Benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one A mixture of ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride (50.0 g, 0.168 mol), formamidine acetate (16.2 g, 0.201 mol), 4.37 M of sodium methoxide in methanol (190 mL) and methanol (200 mL) was heated at 85 C. for 16 hour in a 350 mL sealed reaction vessel. The mixture was allowed to cool and concentrated in vacuo. The residue was dissolved in 1N NaOH (150 mL) and poured over ice. Glacial acetic acid was added to the mixture until the pH of the mixture was 7 and a tan solid precipitated out. The solid was filtered, washed with water and cold ether, and dried on high vacuum to yield the title compound as a tan solid (26.2 g, 61.4%).LC-MS: 242.2 [M+1]+; 1H NMR (400 MHz, DMSO-d6): delta 2.29 (t, 2H, J=5.8 Hz), 2.61 (t, 2H, J=5.8 Hz), 3.26 (s, 2H), 3.64 (s, 2H), 7.21-7.36 (m, 6H), 7.96 (s, 1H). | |
61.4% | INTERMEDIATE 1 6-Benzyl-5,6,7,8-tetrahydropyrido [4,3-d] pyrimidin-4(3H)-one[00273] A mixture of ethyl l-benzyl-4-oxopiperidine-3-carboxylate hydrochloride (50.0 g,0.168 mol), formamidine acetate (16.2 g, 0.201 mol), 4.37 M of sodium methoxide in methanol (190 mL) and methanol (200 mL) was heated at 85 0C for 16 hour in a 350 mL sealed reaction vessel. The mixture was allowed to cool and concentrated in vacuo. The residue was dissolved in IN NaOH (150 mL) and poured over ice. Glacial acetic acid was added to the mixture until the pH of the mixture was 7 and a tan solid precipitated out. The solid was filtered, washed with water and cold ether, and dried on high vacuum to yield the title compound as a tan solid (26.2 g, 61.4 %).MS: 242.2 [M+l]+; 1H NMR (400 MHz, DMSO-d6): 2.29 (t, 2H, J = 5.8 Hz), 2.61 (t, 2H, J = 5.8 Hz), 3.26 (s, 2H), 3.64 (s, 2H), 7.21-7.36 (m, 6H), 7.96 (s, IH). |
55% | With sodium methylate; In methanol; at 70℃; for 18.0h; | To a solution of ethyl l-benzyl-4-oxopiperidine-3-carboxylate hydrochloride (1.0 g, 3.4 mmol) and formamidine acetate (0.420 g, 4.03 mmol) in MeOH (6.7 mL) was added NaOMe in MeOH (4.6 ml, 20 mmol) and the resulting suspension was stirred at 70 C for 18 h. The mixture was cooled to RT and concentrated under reduced pressure. The residue was partitioned between water (1 mL) and 3: 1 CHCh:iPrOH (3 mL). The layers were separated and the organic layer was washed with brine (1 mL), dried over Na2S04 and concentrated under reduced pressure to afford the title compound (444 mg, 55%) as a light yellow solid.MS (ES+) C14H15N3O requires: 241, found: 242 [M+H]+. |
With sodium alcoholate; In ethanol; for 2.0h;Reflux; | Step A:l-Benzyl-3-ethoxycarbonyl-4-piperidone hydrochloride (12.89 g, 43.3 mmol) was suspended in a sodium methoxide solution in methanol (25 % wt/wt, 50 mL, 216. 2 mmol) and formamidine acetate (5.4 g, 51.9 mmol) was added to the mixture. The reaction mixture was refluxed until all of the starting material was consumed (2 h). The methanol was removed under reduced pressure, and the resulting white solid was dissolved in a 3/1 mixture of chloroform / isopropanol. The mixture was washed with water and brine, dried over Na2S04, filtered and evaporated to give the desired product as a white solid (9.4 g). MS (ESEI): 242.1 [M+l]+ | |
With sodium alcoholate; In water; for 2.0h;Reflux; | l-Ben2yl-3-ethoxycarbonyl-4-piperidone hydrochloride (12.89 g, 43.3 mmol) was suspended in a sodium methoxide solution in methanol (25 % wt wt, 50 mL, 216. 2 mmol) and formamidine acetate (5.4 g, 51.9 mmol) was added to the mixture. The reaction mixture was refluxed until all of the starting material was consumed (2 h). The methanol was removed under reduced pressure, and the resulting white solid was dissolved in a 3/1 mixture of chloroform / isopropanol. The mixture was washed with water and brine, dried over Na2SC>4, filtered and evaporated to give the desired product as a white solid (9.4 g). MS (ESEI): 242.1 [M+l]? |
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