Abstract
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.
