1,5-BENZODIAZOCINES

The syntheses of 2-(3-aminopropylamino)-5-chlorobenzophenones 2 and 9 and their intramolecular dehydrations to give 8-chloro-1,2,3,4-tetrahydro-6-phenyl-1,5-benzodiazocines 3 and 10 were effected. A procedure purported to yield a 8-chloro-3,4-dihydro-1,5-benzodiazocin-2-one has been found in fact to give a dimer. This procedure has been successfully utilized in the synthesis of 8-chloro-3,4-dihydro-1-methyl-6-phenyl-1,5-benzodiazocin-2(1H)-one 19, which has been structurally related to 10. A rationale for the anomalous results of this reaction is offered. © 1969, American Chemical Society. All rights reserved.