Vilazodone → 3-(4-oxobutyl)-1H-indole-5-carbonitrile

HRID 1056543

Reaction equation

HRID 1056543 reaction equation
C1C(C#N)=CC2C(CCCCN3CCN(C4C=CC5OC(C(N)=O)=CC=5C=4)CC3)=CNC=2C=1.[OH:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([C:48]#[N:49])[CH:46]=2)[NH:41][CH:40]=1>CS(C)=O>[O:34]=[CH:35][CH2:36][CH2:37][CH2:38][C:39]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([C:48]#[N:49])[CH:46]=2)[NH:41][CH:40]=1

Participants

4

Reactant 2

HCID 6918314VilazodoneHCID 121509853-(4-Hydroxybutyl)-1H-indole-5-carbonitrile

Product 1

HCID 177480653-(4-oxobutyl)-1H-indole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

According to another synthetic process described in US'916 patent, vilazodone is prepared by reacting 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile with sulfur trioxide/pyridine complex in dimethylsulfoxide to produce a reaction mass, followed by customary work up and then concentrating the resulting mass to produce an oily residue. The resulting residue is then chromatographed on silica gel using a mixture of dichloromethane and methyl tert-butyl ether to produce 3-(4-oxobutyl)-1H-indole-5-carbonitrile. The oxobutyl compound is reacted with 5-(1-piperazinyl)benzofuran-2-carboxamide in the presence of sodium cyanoborohydride to produce vilazodone free base, which is further treated with aqueous hydrochloric acid to produce vilazodone hydrochloride.

Workup

  1. customis prepared
  2. customto produce a reaction mass
  3. concentrationconcentrating the resulting mass
  4. customto produce an oily residue
  5. customThe resulting residue is then chromatographed on silica gel using
  6. additiona mixture of dichloromethane and methyl tert-butyl ether

Sources & evidence

ORD record
ord-4e785f5ef8514b6985af6e7f5bbba3b2
Source dataset
uspto-grants-2016_07
Patent number
US09399630B2

Linked notes

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