Water → HCID 23312235, compound

Participants

Reaction Steps

A solution of 14.5 g of 1-(cyclopropylcarbonyl)-4-(2-benzofuranyl)-piperidine in 100 ml of tetrahydrofuran is added dropwise to a refluxing solution of 13.5 g of lithium aluminium hydride in 200 ml of tetrahydrofuran. After 15 hours' refluxing, the reaction mixture is cooled, and the excess lithium aluminium hydride broken down at -10° by means of 15 ml of water, 15 ml of 10% sodium hydroxide solution and 45 ml of water. The reaction solution is filtered off under suction and the filter residue subsequently washed with 1 liter of chloroform; the combined filtrates are then concentrated in vacuo. The residue is dissolved in 500 ml of 2 N hydrochloric acid, and the acid solution washed with ether. The aqueous solution is thereupon adjusted by addition of 10% sodium hydroxide solution to pH 12, and extracted with 1 liter of chloroform. The chloroform solution is dried with sodium sulphate, filtered off with suction, and concentrated by evaporation to obtain crude 1-(cyclopropylmethyl)-4-(2-benzofuranyl)-piperidine. After recrystallisation from hexane, the free base melts at 68°. The hydrochloride is prepared with hydrogen chloride in ethyl acetate, and recrystallised from ethyl acetate, whereupon it melts at 223°-225°.

Provenance & Evidence