Hydrochloric Acid → Benzyl Alcohol

HRID 1049069Notes

Reaction equation

HRID 1049069 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].[CH:35]([OH:38])([CH3:37])C>C(O)C1C=CC=CC=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:38])[C:37]1[CH:5]=[CH:4][CH:3]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 6918314Vilazodone

Product 2

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

Reagents, catalysts & solvents 1

HCID 244Benzyl AlcoholSolvent

Conditions

Temperature
22.5 °C

Procedure

1-[4-(5-Cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine (1 g) in benzyl alcohol (5 ml) was heated under inert gas atmosphere to 45° C. To the suspension was added HCl in isopropanol (0.55 g, 1.2 eq) followed by cooling to 20-25° C. and stirring for about 20 h. The suspension was heated to 35° C. and maintained for 3 h. The solid was filtered, washed with MTBE (2×5 ml) and dried at 65° C. to afford 0.94 g hemi solvate of 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine hydrochloride with benzyl alcohol.

Workup

  1. temperatureThe suspension was heated to 35° C.
  2. temperaturemaintained for 3 h
  3. filtrationThe solid was filtered
  4. washwashed with MTBE (2×5 ml)
  5. customdried at 65° C.

Sources & evidence

ORD record
ord-5bdadfdaa0624b57b1307f13071382a3
Source dataset
uspto-grants-2016_07
Patent number
US09382233B2

Reaction notes

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