Potential metabolites of the noncataleptic neuroleptics: Synthesis of 2-chloro-6-hydroxy(and methoxy)-10-[4-(2-hydroxyethyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin

Author:

Protiva Miroslav,Šedivý Zdeněk,Pomykáček Josef,Bártl Václav,Holubek Jiří,Svátek Emil

Abstract

[5-Chloro-2-(2-methoxyphenylthio)phenyl]acetic acid (VI), obtained via the acetophenone derivative IV, was cyclized to 2-chloro-6-methoxydibenzo[b,f]thiepin-10(11H)-one (VIIIa). 2,10-Dichloro-6-methoxy-10,11-dihydrodibenzo[b,f]thiepin (Xa) was prepared via the alcohol IXa and its substitution reaction with 1-(2-hydroxyethyl)piperazine gave the compound III. Demethylation with boron tribromide in chlorobenzene resulted in the title compound II which is a potential metabolite of the noncataleptic neuroleptic agent docloxythepin.

Publisher

Institute of Organic Chemistry & Biochemistry

Subject

General Chemistry

Cited by 8 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Compounds Derived from Acetic Acid;Aromatic Hydroxyketones: Preparation and Physical Properties;2011

2. Compounds derived from acetic acid;Handbook of Hydroxyacetophenones: Preparation and Physical Properties;2005

3. The place of dibenzo[b,f]thiepin derivatives in medicinal chemistry: Structures and activities;Journal of Heterocyclic Chemistry;1996-05

4. Fifty years in chemical drug research;Collection of Czechoslovak Chemical Communications;1991

5. Potential antidepressants: 6-(Aminoalkoxy)dibenzo[b,f]thiepin-10(11H)-ones and 6-(aminoalkoxy)-10,11-dihydrodibenzo[b,f]thiepin-10-ols;Collection of Czechoslovak Chemical Communications;1989

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