Synthesis and NMR Studies of Z- and E-Isomers of 10-Oxo and 10-Hydroxy Derivatives of Amitriptyline and Nortriptyline.

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Abstract
The N,N-dimethyl and N-methyl derivatives of (Z)- and (E)-(10,11-dihydro-10-hydroxy-5H-dibenzo[a,d]cycloheptene)-.DELTA.5,.gamma.-propylamine [antidepressants] were synthesized from the 10-oxo isomers of the N,N-dimethyl derivatives with conservation of the geometrical configuration. Structural assignments were based upon chemical shift displacement of the aromatic protons by addition of tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium. The presence of solvent dependent equilibria of intramolecular H-bonded and non-H-bonded conformations of the Z-hydroxy isomers were demonstrated by 1H and 13C NMR spectra.

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