新アルキル化反応(第5報) : カルボン酸エステルによる新メチル化反応 : カルボン酸メチルエステルによる2級アミンのN-メチル化反応 : (複素環式化合物の合成研究 第200報)

抄録

In the reaction between secondary amines and methyl carboxylate that between secondary amines like 1, 2, 3, 4-tetrahydroisoquinoline (I) and N-methylbenzylamine (II) and methyl ester of aliphatic carboxylic acids like dimethyl oxalate (VIII) and dimethyl fumarate (IX) afforded amides as the main product, with by-product formation of tertiary amines and quarternary ammonium compounds. On the contrary, in the reaction of I and II with methyl esters of aromatic carboxylic acids like methyl o-nitrobenzoate (VI) and methyl benzoate (VII), and of 1, 2, 3, 4-tetrahydroquinoline (III), N-methylaniline (IV), and diphenylamine (V) with VIII and IX, the main products were tertiary amines and quarternary ammonium compounds, and amides were obtained as a by-product. It was also found that the reaction of III and IV with VII afforded only the tertiary amines.