Benzoyl chloride → N-benzoyl-4-hydroxypiperidine

Participants

Reaction Conditions

Reaction Steps

In a four necked round bottom flask, under Argon atmosphere, 4-hydroxypiperidine (5.32 g, 52.6 mmol) was dissolved in CH2Cl2 (28 mL) and pyridine (28 mL). After cooling at 0° C., benzoyl chloride (6.4 mL, 55.2 mmol), dissolved in CH2Cl2 (7 mL) was drop wise added. The ice bath was removed and the mixture stirred 3 h at rt. The solid was filtered-off and the solvent removed under vacuum. Purification by typical column chromatography, eluting with CH2Cl2/MeOH (20:1) afforded the title compound (7.6 g, 70%) as pale yellow oil. Rf=0.21 (CH2Cl2/MeOH 20:1). MS (ESI) m/z: 206 [M−H]+. FTIR (cm−1): 3349, 3065, 3033, 3005, 2934, 2845, 1607, 1574, 1453, 1365, 1339, 1273, 1238, 1180, 1077, 998, 788, 730, 688.

Provenance & Evidence