Hydrochloric Acid → HCID 20225285, compound

Participants

Reaction Steps

To a stirred solution of N-[2-(4-methylaminocarbonylmethoxyphenyl)-1-methylethyl]-2-methoxy-2-(3-chlorophenyl)ethanamine (0.50 g; 85:15 mixture of diastereoisomers) in dry tetrahydrofuran (20 ml) was added borane-methyl sulphide complex (2 ml), under nitrogen. The solution was boiled under reflux for 3 hours, and after cooling to room temperature, methanol (6 ml) was added. This solution was allowed to stand overnight at room temperature, boiled under reflux for 1 hour, cooled, and hydrogen chloride gas passed through for 10 minutes. After dilution with diethyl ether, cooling to 0° C. and filtering, N-[2-(4-(2-methylaminoethoxy)phenyl)-1-methylethyl]-2-methoxy-2-(3-chlorophenyl)ethanamine dihydrochloride, mp 270°-273° C. (methanol-ethyl acetate), was obtained as a single diastereoisomer.

Provenance & Evidence