Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Vilazodone | HCID 6918314 | — |
| Edukt | 3-(4-Hydroxybutyl)-1H-indole-5-carbonitrile | HCID 12150985 | — |
| Lösungsmittel | Dimethyl Sulfoxide | HCID 679 | — |
| Produkt | 3-(4-oxobutyl)-1H-indole-5-carbonitrile | HCID 17748065 | — |
Reaktionsschritte
According to another synthetic process described in US'916 patent, vilazodone is prepared by reacting 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile with sulfur trioxide/pyridine complex in dimethylsulfoxide to produce a reaction mass, followed by customary work up and then concentrating the resulting mass to produce an oily residue. The resulting residue is then chromatographed on silica gel using a mixture of dichloromethane and methyl tert-butyl ether to produce 3-(4-oxobutyl)-1H-indole-5-carbonitrile. The oxobutyl compound is reacted with 5-(1-piperazinyl)benzofuran-2-carboxamide in the presence of sodium cyanoborohydride to produce vilazodone free base, which is further treated with aqueous hydrochloric acid to produce vilazodone hydrochloride.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US09315456B2 |
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| Quelldatensatz | uspto-grants-2016_04 |
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| ORD ID | ord-99d2ce866f5848d4aa0c99e7aa9e3d22 |
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| Quellennotiz | uspto-grants-2016_04 |
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