19711-54-7Relevant academic research and scientific papers
FLUORINATED TRICYCLIC NEUROLEPTICS WITH PROLONGED ACTION: 7-FLUORO-11--2-ISOPROPYL-10,11-DIHYDRODIBENZOTHIEPIN
Protiva, Miroslav,Jilek, Jiri,Rajsner, Miroslav,Pomykacek, Josef,Ryska, Miroslav,et al.
, p. 698 - 722 (2007/10/02)
Substitution reaction of 11-chloro-7-fluoro-2-isopropyl-10,11-dihydrodibenzothiepin with 1-(2-hydroxyethyl)piperazine gave the title compound I which proved a very potent and long acting 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 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 isofloxithepin (I).
