Ethyl bromoacetate → Ethyl 2-{4-[5-bromo-3-(tert-butyl)-2-methoxyphenyl]piperazino}acetate

HRID 1295979Notes

Reaction equation

HRID 1295979 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+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CN(C)C=O.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]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:12][CH2:13]2)[CH:7]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 589099601-(5-Bromo-3-(tert-butyl)-2-methoxyphenyl]piperazine

Product 1

HCID 22929902Ethyl 2-{4-[5-bromo-3-(tert-butyl)-2-methoxyphenyl]piperazino}acetateYield 75%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-[5-Bromo-3-(tert-butyl)-2-methoxyphenyl]piperazine (750 mg), potassium carbonate (411 mg) and ethyl bromoacetate (0.27 ml) were stirred in dimethylformamide (4 ml) at room temperature for one day. The reaction mixture was diluted with ethyl acetate, the insoluble portion was filtered off and then the concentrated residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (715 mg) as a light red oil (75%).

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-e8469b911ffb44f082961f01d2b5dd8c
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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