Ammonia → Vilazodone

HRID 628801Notes

Reaction equation

HRID 628801 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]C)=O)=[CH:27][C:26]=3[CH:34]=2)[CH2:18][CH2:17]1)#[N:2].[NH3:35]>>[CH:11]1[C:3]([C:1]#[N:2])=[CH:4][C:5]2[C:6]([CH2:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:23]=[CH:24][C:25]5[O:29][C:28]([C:30]([NH2:35])=[O:32])=[CH:27][C:26]=5[CH:34]=4)[CH2:18][CH2:17]3)=[CH:7][NH:8][C:9]=2[CH:10]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 19438830Vilazodone methyl ester

Product 1

HCID 6918314Vilazodone

Conditions

Temperature
27.5 °C

Procedure

Methyl 5-[4-[4-(5-cyanoindol-3-yl)butyl]piperazin-1-yl]benzofuran-2-carboxylate (41 g) was added to saturated methanolic ammonia solution (8200 ml) under stirring at 25-30° C., the resulting mixture was stirred for 3 to 4 hours at the same temperature to form a clear solution. The reaction mass was stirred for 24 hours at 25-30° C., followed by filtration of the separated solid and then dried to produce 28 g of vilazodone. The mother liquors were taken and the solvent was distilled off under vacuum until the solvent quantity reaches around 1200 ml of the initial volume. The resulting mass was cooled to 25-30° C., followed by filtration and then drying to produce 11 g of Vilazodone (Purity by HPLC: 99.5%; Yield: 98.5%).

Workup

  1. stirringthe resulting mixture was stirred for 3 to 4 hours at the same temperature
  2. customto form a clear solution
  3. stirringThe reaction mass was stirred for 24 hours at 25-30° C.
  4. filtrationfollowed by filtration of the separated solid
  5. customdried

Sources & evidence

ORD record
ord-8221e054fd98408bbddf281de4146464
Source dataset
uspto-grants-2016_04
Patent number
US09315456B2

Reaction notes

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