Collect. Czech. Chem. Commun.
1980, 45, 2688-2694
https://doi.org/10.1135/cccc19802688
Fluorinated analogues of tricyclic neuroleptics: 6,9-difluoro derivative of 10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin
Irena Červená, Marta Hrubantová, Emil Svátek, Jiří Holubek, Miroslav Ryska, Jiřina Metyšová and Miroslav Protiva
Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3
Abstract
The acid VI, obtained from 2,5-difluorothiophenol (IV) and (2-iodophenyl)acetic acid, afforded by cyclization with polyphosphoric acid 6,9-difluorodibenzo[b,f]thiepin-10(11H)-one (VII) in a satisfactory yield. Two further steps led to the chloro derivative X giving by a substitution reaction with 1-methylpiperazine the title compound III. This substance exhibits some 10% incoordinating activity of the unsubstituted compound I and an indication of cataleptic activity, in contrast to the inactive analogous dichloro compound II. The bulky atom of chlorine in the vicinity of the methylpiperazine residue interferes evidently with the CNS activity; the influence of the atom of fluorine is much less pronounced in this line.
