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US 6,441,165 B2Granted
Process for the preparation of 11-amino-3-chloro-6, 11-dihydro-5, 5-dioxo-6-methyl-dibenzo[c,f][1,2]thiazepine and application to the synthesis of tianeptine
AssigneeLes Laboratories Servier
InventorsJacky Blanchard, Hugues Turbe, Daniel Brigot
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Abstract
Process for the industrial synthesis of the compound of formula (I): and its addition salts. Application to the synthesis of tianeptine and its pharmaceutically acceptable salts.
Claims2
A process for the industrial synthesis of 11-amino-3-chloro-6,11-dihydro-5,5dioxo- 6-methyl-dibenzo[c,f][1,2]thiazepine of Formula (I):
- and its addition salts, wherein the ketone of Formula (III):
- is reacted with sodium borohydride, in a two-phase medium (chlorinated solvent selected from chloroform, dichloromethane/aqueous sodium hydroxide solution), in the presence of N-dodecyl-N-methyl-diethanolammonium bromide, to yield the alcohol of Formula (IV):
- which, as a suspension in a chlorinated solvent selected from chloroform or dichloromethane, is treated with gaseous hydrogen chloride to yield the chloride of Formula (V):
- which is then, without being isolated, treated with gaseous ammonia, while maintaining the temperature between 25 and 35° C., to yield the compound of Formula (I),
- which is, if desired, converted into an addition salt.
2 more elements
Dependencies are inferred from the claim text.