N-Piperonyl analogue of the atypical antipsychotic clozapine

The crystal structure of 11-[4-(1,3 -benzodioxol-5-ylmethyl)-piperazino]- 8 -chloro-5H-dibenzo [b,e][1,4]diazepine, C25H23-ClN4O2, confirms the buckled nature of the dibenzodiazepine nucleus, with the central seven-membered he terocycle in a boat conformation and the dihedral angle between the planes of the aromatic rings being similar to that found for the parent compound, clozapine, The piperazine ring displays an almost perfect chair conformatio n, with the piperonyl group assuming an equatorial orientation. The relativ e position of the dibenzodiazepine and piperazine ring systems is controlle d by the planarity of the piperazine N atom in the amidine moiety.