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■ Synthesis of 1,2,3,4,4a,5,9,10,16,16a-Decahydro-2-methyl[1]benzazepino [3,2,1-jk]Pyrido[3,4-b][1]benzazepine: A Conformationally Rigid Imipramine Analog

Philip G. Dunber and Arnold R. Martin

*Department of Pharmaceutical Sciences, College of Pharmacy, The University of Arizona, Tucson, AZ 85721, U.S.A.

Abstract

Ortho lithiations and acylations of 10,11-dihydro-5H-dibenz[b,f]azepine and N,N-diethylnicotinamide respectively led to the convenient synthesis of the key intermediate 4-[(10,11-dihydro-5H-dibenz[b,f]azepin-4-yl)hydroxymethyl]-N,N-diethylnicotinamide 2a, Catalytic reduction of 2, and subsequent cyclization of the resulting carboxylic acid 3, provided the pentacyclic lactam 4 required for further elaboration of the rigid imipramine analog. Difficulties in amide hydrolysis are discussed. Further reductions and N-methylation provided both cis and trans ring fusion isomers 8a and 8b identified by ¹H and ¹³C nmr.