Synthesis of N-Substituted (6-Benzyl-4,4-dimethyl-2-cyclohexenyl)-methylamines and Related Compounds

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In a search for synthetic non-narcotic analgesics, 1,6-trans-N-substituted (6-benzyl-4,4-dimethyl-2-cyclohexenyl) methylamines (5) were prepared by dehydration of the corresponding 2,3-trans-2-aminomethyl-3-benzylcyclohexanols (2 and 3) with thionyl chloride. The (1-cyclohexenyl) methylamines (4) and the 1,2-trans-(2-chlorocyclohexyl) methylamines (6) were also produced from the 1,2-cis-cyclohexanols (2) as minor products, but the only isolable by-product from the 1,2-trans-cyclohexanols (3) was the 1,2-cis-(2-chlorocyclohexyl) methylamines (7). The 1,6-cis-(6-benzyl-2-cyclohexenyl) methylamine (13a) was obtained by isomerization of the 2,3-trans-3-benzyl-2-dimethylaminomethylcyclohexanone (1a) followed by reduction and dehydration. Catalytic hydrogenation of (2-benzyl-2-cyclohexenyl) methylamines (17) gave the 1,2-trans-and 1,2-cis-cyclohexylmethylamines (8 and 19). Among the compounds tested, 1,6-trans-N, N-dimethyl-(6-benzyl-4,4-dimethyl-2-cyclohexenyl) methylamine (5a) hydrochloride was as potent as codeine phosphate in analgesic activity as determined by the phenylquinone writhing method.
公益社団法人日本薬学会の論文
1984-01-25