Acetone → HCID 11453886, compound

HRID 1170862Notes

Reaction equation

HRID 1170862 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]([NH2:32])=[O:31])=[CH:27][C:26]=3[CH:33]=2)[CH2:18][CH2:17]1)#[N:2].Cl.CC(C)=[O:37]>CS(C)=O>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:37])[CH: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]([NH2:32])=[O:31])=[CH:27][C:26]=3[CH:33]=2)[CH2:20][CH2:21]1)#[N:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric Acid2×HCID 6918314Vilazodone

Product 1

HCID 11453886HCID 11453886, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.78 g (10 mmol) of 5-{4-[4-(5-cyano-3-indolyl)butyl]-1-piperazinyl}benzo-furan-2-carboxamide are dissolved in 28.4 ml of hot DMSO. After cooling to room temperature, 66.4 ml of conc. HCl are added dropwise with stirring. The batch temperature is held at 24° C. by cooling by means of an ice bath. When the addition of HCl is complete, the batch is stirred at room temperature for 10 h. The crystal slurry is subsequently stirred with 50 ml of acetone, filtered off with suction and rinsed with acetone, isopropanol and diethyl ether. The resultant crystals were dried in air.

Workup

  1. customis held at 24° C.
  2. temperatureby cooling by means of an ice bath
  3. stirringthe batch is stirred at room temperature for 10 h
  4. filtrationfiltered off with suction
  5. washrinsed with acetone, isopropanol and diethyl ether
  6. customThe resultant crystals were dried in air

Sources & evidence

ORD record
ord-ca563e885c6a47a0aee59d45eddfd181
Source dataset
uspto-grants-2010_11
Patent number
US07829565B2

Reaction notes

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