Benzyl Alcohol → Benzyl Alcohol

HRID 1049074Notes

Reaction equation

HRID 1049074 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
22.5 °C

Procedure

1-[4-(5-Cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine (4 g) in benzyl alcohol (36 ml) was heated to 35-40° C. under inert gas atmosphere. The clear solution was filtered through microfiber paper and washed with benzyl alcohol (4 ml). The filtrate was stirred at 20-25° C. for about 30 minutes. To the thin suspension was charged conc. HCl (0.91 g, 0.98 eq.) and 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 6.5 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 (8 ml) and MTBE (3×8 ml) and dried in vacuo at 35-40° C. for about 3 hours to afford 4.5 g mono solvate of 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine hydrochloride with benzyl alcohol.

Workup

  1. filtrationThe clear solution was filtered through microfiber paper
  2. washwashed with benzyl alcohol (4 ml)
  3. customa clear solution was obtained
  4. stirringFollowing stirring for about 10 minutes a thick suspension
  5. customformed
  6. stirringto stir at 20-25° C. for 17 hours
  7. temperatureThe suspension was heated to about 95° C.
  8. stirringstirred for about 6.5 hours whereupon the suspension
  9. temperatureThe resulting suspension was cooled to 30-35° C.
  10. stirringstirred for about 1 hour
  11. filtrationThe solid was filtered
  12. washwashed with benzyl alcohol (8 ml) and MTBE (3×8 ml)
  13. customdried in vacuo at 35-40° C. for about 3 hours

Sources & evidence

ORD record
ord-b66ab48cdb4d4d459e076c7cad2f8df1
Source dataset
uspto-grants-2016_07
Patent number
US09382233B2

Reaction notes

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