3-Chloro-1-propanol → 4-(p-Fluorobenzoyl)-1-(3-hydroxypropyl)piperidine

Participants

Reaction Steps

A mixture of 24.3 g. (0.1 mole) of 4-(p-fluorobenzoyl)-piperidine hydrochloride, 12.5 g. (0.125 mole) of 3-chloropropanol and 42.0 g. (0.5 mole) of sodium bicarbonate in 500 ml. of n-butanol was stirred at reflux for 15 hours. An additional 3.0 g. (0.025 mole) of 3-chloropropanol was added after thin layer chromatography showed incomplete reaction and the reaction was continued for 3 hours. The cooled reaction mixture was filtered, the filtrate concentrated at reduced pressure and the residual oil crystallized by trituration in isopropyl ether. The tan solid weighed 23 g. (87%) and melted at 107°-109° C. Recrystallization from benzene-isooctane gave 17.7 g. of material melting at 111°-112° C.

Provenance & Evidence