Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl Alcohol | HCID 244 | — |
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Vilazodone | HCID 6918314 | — |
| Product | Benzyl Alcohol | HCID 244 | — |
| Product | 2-benzofurancarboxamide, 5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)-1-piperazinyl)-, hydrochloride (1:1) | HCID 6918313 | — |
Reaction Steps
1-[4-(5-Cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine (25 g) was suspended in benzyl alcohol (250 ml) under inert gas atmosphere. The resulting suspension was charged with conc. HCl (0.91 g, 0.98 eq.) and after addition a clear solution was obtained. Following stirring for about 10 minutes a thick suspension formed, which was allowed to stir at 20-25° C. for 17 hours. The suspension was heated to about 95° C. and stirred for about 5 hours whereupon the suspension became thin. The resulting suspension was cooled to 30-35° C. and stirred for about 1 hour. The solid was filtered, washed with benzyl alcohol (50 ml) and MTBE (2×50 ml) and dried in vacuo at 20-25° C. for about 3 hours to afford 31.5 g mono solvate of 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine hydrochloride with benzyl alcohol.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09382233B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-50608de70bb141bdacef970780c6e5b6 |
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| Source note | uspto-grants-2016_07 |
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