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Facile Syntheses of the Three Major Metabolites of Thioridazine

✍ Scribed by Ryan J. Morrow; Jeff S. Millership; Paul S. Collier

Publisher
John Wiley and Sons
Year
2005
Tongue
German
Weight
172 KB
Volume
88
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Efficient, mild syntheses of the three major metabolites 2–4 of the important antipsychotic drug thioridazine (1) have been developed. The cardiotoxic metabolite 2 with a ring sulfoxide moiety was prepared in 96% yield by oxidation of 1 with NaIO~4~ under acidic conditions. Four different procedures were elaborated for the selective side‐chain sulfide oxidation of 1 to mesoridazine (3), giving rise to yields of up to 91%. Finally, sulforidazine (4) was synthesised via oxidation of the sulfoxide 3 in the presence of either KMnO~4~ or t‐BuOOH under basic conditions. Except for the oxidation with t‐BuOOH, all reactions took place under mild conditions within a few minutes, were nicely reproducible, and afforded medium‐to‐high yields of the desired products, which could be readily purified by column chromatography.

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