4-Phenylpiperidine → 1-(1-Naphthoxy)-3-(4-phenylpiperidino)-2-propanol

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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-phenylpiperidine. The resulting mixture is then refluxed for 24 hours. Evaporation of the solvent from the reaction mixture under reduced pressure affords 1-(1-naphthoxy)-3-(4-phenylpiperidino)-2-propanol. This free amine is then 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 ethanol and ethyl ether to give 1-(1-naphthoxy)-3-(4-phenylpiperidino)-2-propanol hydrochloride. This compound melts at 195°-197° C. and is represented by the following structural formula ##STR6##

Provenance & Evidence