Synthesis of 2-Aminomethyl-3-benzyl-5,5-dimethylcyclohexanones

概要

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As part of our search for synthetic non-narcotic analgesics, 2-(substituted) aminomethyl-3-benzyl-5,5-dimethylcyclohexanones (3) were prepared by the Mannich reaction of 5,5-dimethylcyclohexanones (2) with secondary amine hydrochlorides. In this reaction, 6-(substituted)-aminomethylcyclohexanones (4) were also obtained as by-products. Reduction of 3 gave the corresponding 2-(substituted) aminomethyl-3-benzylcyclohexanols (5 and 6). The configurations of compounds 3,5 and 6 were determined to be 2,3-trans, 1,2-cis-2,3-trans, and 1,2-trans-2,3-trans, respectively, by analysis of the nuclear magnetic resonance spectral data. Among the tested compounds, 2,3-trans-3-benzyl-and 3-(3-methoxybenzyl)-2-dimethylaminomethyl-5,5-dimethylcyclohexanones (3a and 3c) were almost as potent as codeine phosphate as regards analgesic activity determined by the phenylquinone writhing method.
公益社団法人日本薬学会の論文
1983-11-25