Water → HCID 23312336, compound

Participants

Reaction Steps

A solution of 19.0 g of 1-(cyclopropylcarbonyl)-4-(5-cyclohexyl-2-benzofuranyl)-piperidine in 150 ml of tetrahydrofuran is added dropwise to a solution, boiling under reflux, of 13.5 g of lithium aluminium hydride in 200 ml of tetrahydrofuran. The reaction mixture is then refluxed for a further 15 hours; it is afterwards cooled, and the unreacted lithium aluminium hydride is decomposed 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 thereupon filtered with suction, the filter residue is washed with 100 ml of chloroform, and the combined filtrates are concentrated in vacuo. The residue is dissolved in 500 ml of 2 N hydrochloric acid, and the acid solution is washed with ether. The aqueous solution is subsequently brought to pH 12 by the addition of 10% sodium hydroxide solution, and extracted with one liter of chloroform. The chloroform solution is dried with sodium sulphate, filtered with suction and concentrated by evaporation to obtain crude 1-(cyclopropylmethyl)-4-(5-cyclohexyl-2-benzofuranyl)-piperidine. This is converted with hydrogen chloride in ethyl acetate into the hydrochloride, and this is recrystallised from ethyl acetate, whereupon it melts at 220°.

Provenance & Evidence