Ammonia → Vilazodone

HRID 628802Notes

Reaction equation

HRID 628802 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]>CO>[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

4

Reactant 2

HCID 222AmmoniaHCID 19438830Vilazodone methyl ester

Product 1

HCID 6918314Vilazodone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-[4-[4-(5-cyanoindol-3-yl)butyl]piperazin-1-yl]benzofuran-2-carboxylate (41 g) was taken in methanol (1000 ml) under stifling at 25-35° C., followed by reacting with ammonia gas for 2 hours under pressure of 4 Kg/cm2. The separated solid was filtered and then dried to produce 32 g of vilazodone. The mother liquors were taken and the solvent was distilled off under vacuum until the solvent quantity reaches around 50 ml of the initial volume. The resulting mass was cooled to 25-30° C., followed by filtration and then drying to produce 6 g of Vilazodone (Purity by HPLC: 99.5%; Yield: 96%).

Workup

  1. customunder stifling at 25-35° C.
  2. filtrationThe separated solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-5178a7548d3d4ffab6c5e7f376351889
Source dataset
uspto-grants-2016_04
Patent number
US09315456B2

Reaction notes

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