Synthesis of N-substituted (6-benzyl-4,4-dimethyl-2-cyclohexenyl)methylamines and related compounds.
書誌事項
- 公開日
- 1984
- 資源種別
- journal article
- DOI
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- 10.1248/cpb.32.44
- 公開者
- 公益社団法人 日本薬学会
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説明
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.
収録刊行物
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- ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ
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ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ 32 (1), 44-54, 1984
公益社団法人 日本薬学会