新アルキル化反応(第4報) : サリチル酸メチルによる2級アミンのN-アルキル化反応 : 複素環式化合物の合成研究第171報

概要

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Fusion reaction of methyl salicylate and secondary amines afforded salicylamide compounds in a low yield only in the case of 1,2,3,4-tetrahydroisoquinoline (I) and piperidine, and the amide compound was not obtained in the case of 1,2,3,4-tetrahydroquinoline (II), N-methylbenzylamine (III), N-methylaniline (IV), and diphenylamine (V), forming N-methylated tertiary amines as the main product. Further, when such tertiary amines were 2-methyl-1,2,3,4-tetrahydroisoquinoline (VII) and N, N-dimethylbenzylamine, quaternary ammonium salicylate was also formed. When the secondary amine was a comparatively strong base like I, salicylate of I was also found to be formed as a by-product.
公益社団法人日本薬学会の論文
1967-03-25