1954 年 74 巻 7 号 p. 723-725
Starting with o-Xylene of approximately 95% purity, it was derived through the chloromethyl compound (II) to the cyanide (III) and condensed with methyl-bis (β-chloro-ethyl) amine, in the presence of sodium amide, to obtain 1-methyl-4-(3′, 4′-dimethylphenyl)-4-cyanopiperidine (IV). Subsequent saponification and esterification yielded ethyl 1-methyl-4-(3′, 4′-dimethylphenyl)-piperidine-(4)-carboxylate (V). On the other hand, (II) was derived through the sulfide (VII and VIII) and the sulfone (IX and X), with subsequent condensation with methyl-bis (β-chloroethyl) amine to 1-methyl-4-(3′, 4′-dimethylphenyl)-piperidine-(4) methyl sulfone (XI) and ethyl sulfone (XII).