反应详情

温度

110 °C

To a solution of 3-benzylpiperidine hydrochloride (2 g, 9.4 mmol) in DMF (40 mL) were added methyl 5-bromovalerate (1.6 mL, 11.3 mmol) and potassium carbonate (3.2 g, 23.6 mmol). This heterogeneous mixture was heated at 110° C. for 1 hr then cooled at 25° C., diluted with water (200 mL) and diethyl ether (200 mL). The aqueous solution was extracted with diethyl ether (100 mL) and the collected organic phase was washed with brine (200 mL), dried and concentrated in vacuum. The crude compound was purified by silica gel column chromatography using CH2Cl2/MeOH as eluant to afford the title compound as an oil (1.76 g, 65%). 1H-NMR (CDCl3): 0.8-1.0 (m, 1H); 1.4-1.7 (m, 8H); 1.8-1.95 (m, 2H); 2.25-2.35 (m, 4H); 2.4-2.6 (m, 2H); 2.75-2.9 (m, 2H); 3.65 (s, 3H); 7.132 (d, J=7.0, 2H); 7.186 (d, J=7.2, 1H); 7.264 (t, J=7.2, 2H).

1. temperaturethen cooled at 25° C.
2. extractionThe aqueous solution was extracted with diethyl ether (100 mL)
3. washthe collected organic phase was washed with brine (200 mL)
4. customdried
5. concentrationconcentrated in vacuum
6. customThe crude compound was purified by silica gel column chromatography