Benzyl Chloride → 2,2'-((Phenylmethyl)imino)bisethanol

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Reaction Steps

Eisleb in Example 2 of U.S. Patent 2,167,351, issued July 25, 1939, shows the preparation of 1-benzyl-4-phenylpiperidine-4-carbonitrile hydrochloride, m.p. 259°-260° C., as an intermediate for normeperidine, namely, ethyl 4-phenylpiperidine-4-carboxylate, by first reacting benzyl chloride with N,N-bis(2-hydroxyethyl)amine to produce N,N-bis(2-hydroxyethyl)benzylamine, next reacting the latter compound with thionyl chloride to produce N,N-bis(2-chloroethyl)benzylamine and isolating it in free base form as "an oil of feebly brownish color"; and then heating N,N-bis(2-chloroethyl)benzylamine with benzyl cyanide (same as phenylacetonitrile) in toluene in the presence of sodium amide (same as sodamide).

Provenance & Evidence