2-4- (4-Bromophenyl) -1H-1, 2, 3-triazol-1-ylmethylphthalimide, C17H11BrN4O, was synthesized by click chemistry employing a copper-catalyzed azide-alkyne 1, 3-dipolar cycloaddition. The molecule adopts an angular structure and was found to crystallize in the monoclinic system (space group P21/n, Z = 4). Reaction with morpholine in the presence of a base afforded 4-4- (4-bromophenyl) -2H-1, 2, 3-triazol-2-ylmethylmorpholine, C13H15BrN4O, as the major product, involving a nucleophilic substitution of morpholine for the phthalimide group and migration of the substituent from N1 to N2 on the 1, 2, 3-triazole ring. The morpholine-substituted compound likewise crystallizes in the monoclinic system (space group P21/c, Z = 4) with the molecule exhibiting an angular shape. Both crystal structures appear to be governed by close packing, with weak C-H. . . O and C-H. . . N hydrogen bonds as the prevailing intermolecular interactions.
Palme et al. (Thu,) studied this question.