1,4-Dihydropyridine의 Dialkylaminomethyl화 유도체의 합성

Dialkylaminomethylation of 1,4-Dihydropyridine

When 2,6-Dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-mono methyl ester(3) was reacted with dimethyl methylene ammonium chloride (5a) and K2CO3 in DMF, 2,6-dimethyl-4-(3''-nitrophenyl)-5-(N,N-dimethylamino)methyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (6a) was obtained in 41% yield. As the same procedure with compound (3) and the other dialkylaminomethylating reagents (5b, c, d, e), 2,6-dimethyl-4-(3''-nitrophenyl)-5-(N,N-diethylamino)methyl-1,4-dihydropyridine-3-carboxylic acid methylester(6b), 2,6-dimethyl-4-(3''-nitrophenyl)-5-(1''-pyrrolidinyl)methyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (6c), 2,6-dimethyl-4-(3''-nitrophenyl)-5-(1''-piperidinyl)methyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (6d) and 2,6-dimethyl-4-(3''-nitrophenyl)-5-(1''-morpholinyl)methyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (6e) were obtained in 28%, 49%, 48% and 18% yield respectively.