Dextro 1-methyl-2-(2-naphthyl) aziridine

摘要

Racemic 1-methyl-2-(2-naphthyl)aziridine, being useful as a tranquilizer, is prepared via three routes: (a) halogenation of the corresponding aminoalcohol and treatment of the resulting haloamine with an alkali; (b) treatment of the corresponding aminoalcohol with sulfuric acid and treatment of the resulting hydrogen sulfate with an alkali; and (c) treatment of 2-(2-naphthyl)aziridine with an oxonium methylating agent. Dextro-1-methyl-2-(2-naphthyl)aziridine, being more potent in the tranquilizing activity than the racemate, is prepared by optical resolution of racemic 2-(2-naphthyl)-2-methylaminoethanol with levo-tartaric acid, treatment of the resulting dextro-2-(2-naphthyl)-2-methylaminoethanol levo-tartrate with an alkali, treatment of the resulting dextro-2-(2-naphthyl)-2-methylaminoethanol with a halogenating agent and treatment of the resulting levo-N-methyl-2-halogeno-1-(2-naphthyl)ethylamine with an alkali.