Abstract
An investigation of Grignard reaction of N-(N', N'-dialkylaminomethyl) amides (N-Mannich base) revealed that the phthalimide and succinimide derivatives underwent nucleophilic attack by Grignard reagent resulting in substitution of the amide residue with alkyls of Grignard reagent, to give tertiary amines in fair yields. These reactions have provided an practical means for preparation of tertiary amines from secondary amines through the N-Mannich bases. In these reactions it was also found that, when more than one molar equivalent amount of Grignard reagent was used, attacks to the amide moieties intially formed proceeded to give phthalimidine derivatives and γ-ketoamide respectively in the case of using N-(N', N'-dialkylaminomethyl) phthalimide and N-(N', N'-dialkylaminomethyl) succinimide. For identities of a series of the γ-ketoamides obtained discussions of their spectral data are also described.
