Improved process for the manufacture of citalopram hydrobromide

Details Improved process for the manufacture of citalopram hydrobromide Improved process for the manufacture of citalopram hydrobromide

C - Chemistry, Metallurgy

07

C

C07C 255/00 (2006.01) C07D 307/78 (2006.01) C07D 307/87 (2006.01)

Patent

CA 2546422

The present invention describes an improved process for the preparation of extremely pure 1-(4'-Fluorophenyl)-1-(3-dimethylaminopropyl)-5- phthalanecarbonitrile and its bromide salt (citalopram hydrobromide), which is a well known antidepressant. Other aspect of the invention are isolation of crystalline (4-Bromo-2-hydroxymethyl)phenyl-(4-fluorophenyl)-3- (dimethylaminopropyl)methanol (Bromodiol) and conversion of desmethylcitalopram which is formed during the cyanide exchange reaction, to Citalopram by heating with a mixture of formaldhyde and formic acid in chloroform. The resulting citalopram is conventionally purified using extraction methodology.

L'invention décrit un procédé amélioré de préparation de 1-(4'-fluorophényl)-1-(3-diméthylaminopropyl)-5-phtalane-carbonitrile extrêmement pur et de son sel de bromure (hydrobromure de citalopram), qui est un antidépresseur bien connu. Un autre aspect de l'invention concerne l'isolement de (4-bromo-2-hydroxyméthyl)phényl-(4-fluorophényl)-3-(diméthylaminopropyl)méthanol (bromodiol) et la conversion du desméthylcitalopram formé pendant la réaction d'échange de cyanure en citalopram par échauffement avec un mélange de formaldéhyde et d'acide formique dans du chloroforme. Le citalopram ainsi obtenu est purifié de manière conventionnelle par une méthodologie d'extraction.

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