Carbon 13 NMR Shift Assignments for E- and Z -Dothiepin Hydrochloride and 6H-Dibenzo[b,e]thiepin-11-One

Abstract

Carbon¹³ chemical shift assignments are reported for Z- and E-dothiepin hydrochloride (N,N-dimethyldibenzo[b,e]thiepin-delta-11(6H)′, gamma-propylamine hydrochloride). The commercial product, a mixture of approximately 95% E-isomer, is of clinical importance as an antidepressant drug. The precursor and degradation product, 6H-dibenzo[b,e]thiepin-11-one, and related model compounds were also studied. Homo- and heteronuclear shift-correlated 2D NMR, selective INEPT, selective and off-resonance decoupling, and inversion-recovery (T₁) experiments as well as model compound comparisons were used in assignments.

Keywords

2D NMR 6H-Dibenzo[b,e]thiepin-11-one Conformation

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References

Barchas

J. D.

Berger

P. A.

Ciaranello

R. D.

, and Elliot

, Psychopharmacology (Oxford University Press, New York, 1977), p. 174–205.

Irwin

W. J.

and Po

L. W.

, Proc. Analyt. Div. Chem. Soc. 329 (1979).

L. W.

and Irwin

W. J.

, J. Pharm. Pharmacol. 32, 25 (1980).

Asscher

Avnir

Rotman

, and Agranat

, J. Pharm. Sci 71, 122 (1980).

Breitmaier

and Voelter

, ¹³C NMR Spectroscopy (Verlag Chemie, New York, 1978), p. 213.

Wehrli

F. W.

and Wirthlin

, Carbon-13 NMR Spectra (Heyden, London, 1978), p. 47.

Hawkins

D. H.

and Midgley

, J. Pharm. Pharmacol. 30, 547 (1978).