2-((1-Naphthalenyloxy)methyl)oxirane → 3-[4-(p-Chlorophenyl)-4-ethoxycarbonylpiperidino]-1-(1-naphthoxy)-2-propanol

Participants

Reaction Steps

To a solution of 5.0 parts of 1,2-epoxy-3-(1-naphthoxy)propane in 79 parts of ethanol is added 5.0 parts of 4-(p-chlorophenyl)-4-ethoxycarbonylpiperidine. The resulting mixture is then refluxed for 24 hours. The solvent is stripped from the reaction mixture under reduced pressure to afford 3-[4-(p-chlorophenyl)-4-ethoxycarbonylpiperidino]-1-(1-naphthoxy)-2-propanol. This material is dissolved in isopropanol and treated with a solution of hydrochloric acid in isopropanol. The resulting salt is separated by filtration and recrystallized from a mixture of isopropanol and ethyl ether to give 3-[4-(p-chlorophenyl)-4-ethoxycarbonylpiperidino]-1-(1-naphthoxy)-2-propanol hydrochloride. This compound exhibits a melting point of 196°-198° C. and is represented by the following structural formula ##STR8##

Provenance & Evidence