Abstract
On the reaction of N-(dialkylaminomethyl) imides and -amides with nucleophiles the previous papers have exhibited the substitution of the imide or the amide residue and that of the dialkylamine residue. Although the actual substitution has been shown to depend on the substrate and the reaction condition, preferential substitution site of the substrate and how this is influenced by the reaction condition have been still in the dark. In pursuit of the substitution reaction of N-(piperidinomethyl) phthalimide, -succinimide and -benzamide it has been presumed that the substitution of the imide or amide residue is processed directly and the substitution of the piperidine residue is processed by succeeding secondary substitution or through elimination of piperidine, if possible, followed by addition of nucleophiles.
