In:
Collection of Czechoslovak Chemical Communications, Institute of Organic Chemistry & Biochemistry, Vol. 51, No. 3 ( 1986), p. 698-722
Abstract:
Substitution reaction of 11-chloro-7-fluoro-2-isopropyl-10,11-dihydrodibenzo[ b,f, ]thiepin with 1-(2-hydroxyethyl)piperazine gave the title compound I which proved a very potent and longacting oral neuroleptic agent (isofloxythepin). Its resolution by means of dibenzoyl-(+)- and -(-)-tartaric acid led to (-)- and (+)-enantiomer out of which the former represents the neuroleptically active component. In the synthetic sequence leading to I , preparation of two key intermediates was re-elaborated using new partial sequences: 4-fluoro-2-iodobenzoic acid ( XIII ) from 4-fluoro-2-nitroaniline ( V ) via the nitrile VI and the acids VIII and XII , and [4-fluoro-2-(4-iso-propylphenylthio)phenyl]acetic acid ( XVIII ) from XIII via XIV and the compounds XV-XVII . The sulfoxides and N-oxides XIX-XXII were prepared as potential metabolites of isofloxythepin ( I ).
Type of Medium:
Online Resource
ISSN:
0010-0765
,
1212-6950
DOI:
10.1135/cccc19860698
Language:
English
Publisher:
Institute of Organic Chemistry & Biochemistry
Publication Date:
1986