Dimethylformamide → 2-{4-[5-Bromo-3-(tert-butyl)-2-methoxyphenyl]piperazino}acetonitrile

HRID 1295972Notes

Reaction equation

HRID 1295972 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:5]([O:14][CH3:15])=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Br[CH2:32][C:33]#[N:34]>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:5]([O:14][CH3:15])=[C:6]([N:8]2[CH2:9][CH2:10][N:11]([CH2:32][C:33]#[N:34])[CH2:12][CH2:13]2)[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 589099601-(5-Bromo-3-(tert-butyl)-2-methoxyphenyl]piperazine

Product 1

HCID 589100312-{4-[5-Bromo-3-(tert-butyl)-2-methoxyphenyl]piperazino}acetonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-[5-bromo-3-(tert-butyl)-2-methoxyphenyl]piperazine (550 mg), potassium carbonate (302 mg), dimethylformamide (7 ml) and bromoacetonitrile (0.12 ml) were combined and the mixture was stirred at room temperature for 4 hours. The reaction mixture was diluted with ethyl acetate, the insoluble portion was filtered off, and the concentrated residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (480 mg) as colorless crystals (78%).

Workup

  1. filtrationthe insoluble portion was filtered off
  2. customthe concentrated residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-91fa5a39439f45648d3494508a4e872e
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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