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US 8,802,851 B2Granted
Process for preparing vilazodone hydrochloride
AssigneeErregierre S.p.A.
InventorsMassimo Ferrari, Daniele De Zani, Matteo Bonaldi
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Abstract
The present invention relates, in a first aspect, to a process preparing vilazodone hydrochloride that comprises the reaction of 3-(4-chloro-1-hydroxy-butyl)-1H-indol-5-carbonitrile with 5-piperazin-1-yl-benzofuran-2-carboxylate methyl hydrochloride with the formation of a 1,4-piperazine, with subsequent dehydration, hydrogenation and treatment with ammonia, to obtain vilazodone in free base form that is then converted into the hydrochloride thereof.
Claims15
A process for preparing vilazodone, or a hydrochloride form thereof comprising the steps of
- A) reacting 3-(4-chloro-1-hydroxy-butyl)-1H-indol-5-carbonitrile of formula (I)
- with 5-piperazin-1-yl-benzofuran-2-carboxylate methyl hydrochloride of formula (II)
- to give 5-{4-[4-(5-cyano-1H-indol-3-yl)-4-hydroxybutyl]-piperazin-1-yl}benzofuran-2-carboxylate methyl of formula (III)
- B) treating the compound of formula (III), obtained from step A, with an acidification agent to obtain 5-{4-[4-(5-cyano-1H-indol-3-yl)-4-hydroxy-butyl]-piperazin-1-yl}benzofuran-2-carboxylate methyl of formula (IV)
- C) hydrogenating the compound of formula (IV) with H2 to obtain 5-{4-[4-(5-cyano-1H-indol-3-yl)-4-hydroxy-butyl]-piperazin-1-yl}benzo-furan-2-carboxylate methyl of formula (V)
- D) treating the compound of formula (V) obtained from step C) with ammonia to obtain 5-(4-[4-(5-cyano-1H-indol-3-yl)butyl]piperazin-1-yl)benzo-furan-2-carboxamide of formula (VI),
- E) optionally treating the compound of formula (VI) with hydrochloride acid to obtain vilazodone hydrochloride of formula (VII)
4 more elements
Dependencies are inferred from the claim text.