Mannich reaction of dihydropyridine derivatives I. Reactions with secondary amines.

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Abstract

Dialkyl 4-aryl-1, 4-dihydro-2, 6-dimethylpyridine-3, 5-dicarboxylates (III) were subjected to the Mannich reaction with excess paraformaldehyde and secondary amine hydrochloride in boiling ethanolic solution. When the compounds III were treated with a 5-to 7-fold molar excess of the aldehyde and amine salt, 2, 6-bis (2-disubstituted aminoethyl)-dihydropyridine derivatives (V) were obtained in good yields. On treatment with a 2- to 3-fold molar excess of the reactants, compounds III were converted to 2-(2-disubstituted aminoethyl)-6-methyldihydropyridine derivatives (IV) and V. When dioxane was used as a solvent with a 6-fold molar excess of the reactants, the tetrakis (dimethylaminomethyl) derivative (VII) was obtained.

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