1-Benzyl-4-(dimethylamino)piperidine

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-amino-1-benzylpiperidine (1.47 g, 7.7 mmol) in CF3 CH2OH (14 ml) were added molecular sieve 4 Å (5), and paraformaldehyde (0.51 g, 17 mmol). After stirring at RT for 1 h, NaCNBH3 (2.5 g, 39.8 mmol) was added and stirred for 16 h at RT. The reaction was stopped by addition of H2O and the product was extracted with (4:1) (Et2O:CH2Cl2). Organic fractions were combined and washed with brine (2×), dried over MgSO4, filtered and concentrated to give a crude material which was purified by silica flash chromatography to afford 4-dimethylamino-1-benzylpiperidine (80% yield). FAB Mass [M+1]+35Cl 219. stirred for 16 h at RT the product was extracted with (4:1) (Et2O:CH2Cl2) washed with brine (2×) dried over MgSO4 filtered concentrated to give a crude material which was purified by silica flash chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-amino-1-benzylpiperidine (1.47 g, 7.7 mmol) in CF3 CH2OH (14 ml) were added molecular sieve 4 Å (5), and paraformaldehyde (0.51 g, 17 mmol). After stirring at RT for 1 h, NaCNBH3 (2.5 g, 39.8 mmol) was added and stirred for 16 h at RT. The reaction was stopped by addition of H2O and the product was extracted with (4:1) (Et2O:CH2Cl2). Organic fractions were combined and washed with brine (2×), dried over MgSO4, filtered and concentrated to give a crude material which was purified by silica flash chromatography to afford 4-dimethylamino-1-benzylpiperidine (80% yield). FAB Mass [M+1]+35Cl 219. stirred for 16 h at RT the product was extracted with (4:1) (Et2O:CH2Cl2) washed with brine (2×) dried over MgSO4 filtered concentrated to give a crude material which was purified by silica flash chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-amino-1-benzylpiperidine (1.47 g, 7.7 mmol) in CF3CH2OH (14 ml) were added molecular sieve 4 Å (5 g), and paraformaldehyde (0.51 g, 17 mmol). After stirring at RT for 1 h, NaCNBH3 (2.5 g, 39.8 mmol) was added and stirred for 16 h at RT. The reaction was stopped by addition of H2O and the product was extracted with (4:1) (Et2O:CH2Cl2). Organic fractions were combined and washed with brine (2×), dried over MgSO4, filtered and concentrated to give a crude material which was purified by silica flash chromatography to afford 4-dimethylamino-1-benzylpiperidine (80% yield). FAB Mass [M+1]+35Cl 219. stirred for 16 h at RT the product was extracted with (4:1) (Et2O:CH2Cl2) washed with brine (2×) dried over MgSO4 filtered concentrated to give a crude material which was purified by silica flash chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of the 1-benzyl-4-dimethylaminopiperidine in 125 ml. of methanol was shaken with 1.0 gm. of 10 percent palladium on carbon under 50 psi of hydrogen at 50°C. until one equivalent of hydrogen was consumed. The suspension was filtered and the filtrate concentrated at atmospheric pressure. The residue was distilled at 20 mm. Hg. to give 4-dimethylaminopiperidine, b.p. 90°-92°C. The suspension was filtered the filtrate concentrated at atmospheric pressure The residue was distilled at 20 mm. Hg

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 0.5 g. of platinum oxide in 25 ml. of ethanol (prereduced as described above) was added a solution of the 1-benzyl-4-methylaminopiperidine and 29.7 ml. of 37 percent aqueous formaldehyde in 60 ml. of ethanol. This suspension was reduced at 50 psi of hydrogen until one equivalent of hydrogen was consumed. The mixture was then filtered and the filtrate concentrated in vacuo. A solution of the residue in benzene was extracted with dilute hydrochloric acid. The aqueous phase was made alkaline with 40 percent aqueous sodium hydroxide and extracted with methylene chloride. The organic layer was dried over anhydrous potassium carbonate and concentrated in vacuo to afford 1-benzyl-4-dimethylaminopiperidine. To a suspension of 0.5 g was consumed The mixture was then filtered the filtrate concentrated in vacuo A solution of the residue in benzene was extracted with dilute hydrochloric acid extracted with methylene chloride The organic layer was dried over anhydrous potassium carbonate concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-amino-1-benzylpiperidine (1.47 g, 7.7 mmol) in CF3 CH2OH (14 ml) were added molecular sieve 4 Å (5), and paraformaldehyde (0.51 g, 17 mmol). After stirring at RT for 1 h, NaCNBH3 (2.5 g, 39.8 mmol) was added and stirred for 16 h at RT. The reaction was stopped by addition of H2O and the product was extracted with (4:1) (Et2O:CH2Cl2). Organic fractions were combined and washed with brine (2×), dried over MgSO4, filtered and concentrated to give a crude material which was purified by silica flash chromatography to afford 4-dimethylamino-1-benzylpiperidine (80% yield). FAB Mass [M+1]+35Cl 219. stirred for 16 h at RT the product was extracted with (4:1) (Et2O:CH2Cl2) washed with brine (2×) dried over MgSO4 filtered concentrated to give a crude material which was purified by silica flash chromatography