Hydrochloric Acid → 1-(2-Diethylaminoethyl)-2-phenyl-5-methyl-4,5,6,7-tetrahydroindole hydrochloride

Participants

Reaction Steps

A solution of 5.94 g (0.05 mole) of 2-diethylaminoethylamine and 11.52 g (0.05 mole) of 4-methyl-2-phenacyl-cyclohexanone in glacial acetic acid is refluxed under nitrogen for 8 hours. Water is added to the mixture, and the mixture is acidified with dilute hydrochloric acid and washed with ether. The aqueous solution is basified with 10% sodium carbonate and extracted with ether to give a light brown oil. The oil is dissolved in ether and ethereal hydrogen chloride is added to give a granular off-white salt. The salt is recrystallized from an isopropanol-ether mixture and then from a methanol-ether pair to give 1-(2-diethylaminoethyl)-2-phenyl-5-methyl-4,5,6,7-tetrahydroindole hydrochloride as light tan crystals, m.p. 171°-177° C.

Provenance & Evidence