Benzyl Alcohol → Benzyl Alcohol

HRID 1049075Notes

Reaction equation

HRID 1049075 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:23]=[CH:24][C:25]3[O:29][C:28]([C:30](=[O:32])[NH2:31])=[CH:27][C:26]=3[CH:33]=2)[CH2:18][CH2:17]1)#[N:2].[ClH:34].[CH2:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[ClH:34].[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([C:22]2[CH:23]=[CH:24][C:25]3[O:29][C:28]([C:30](=[O:32])[NH2:31])=[CH:27][C:26]=3[CH:33]=2)[CH2:20][CH2:21]1)#[N:2].[CH2:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 6918314Vilazodone

Product 2

HCID 244Benzyl AlcoholHCID 69183132-benzofurancarboxamide, 5-(4-(4-(5-cyano-1H-indol-3-yl)butyl)-1-piperazinyl)-, hydrochloride (1:1)

Conditions

Temperature
95 °C

Procedure

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.

Workup

  1. additionafter addition a clear solution
  2. customwas obtained
  3. customformed
  4. stirringto stir at 20-25° C. for 17 hours
  5. stirringstirred for about 5 hours whereupon the suspension
  6. temperatureThe resulting suspension was cooled to 30-35° C.
  7. stirringstirred for about 1 hour
  8. filtrationThe solid was filtered
  9. washwashed with benzyl alcohol (50 ml) and MTBE (2×50 ml)
  10. customdried in vacuo at 20-25° C. for about 3 hours

Sources & evidence

ORD record
ord-50608de70bb141bdacef970780c6e5b6
Source dataset
uspto-grants-2016_07
Patent number
US09382233B2

Reaction notes

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