Potassium Carbonate → 4-[Ethoxycarbonyl-(3-trifluoromethyl-phenyl)-methyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 550841Notes

Reaction equation

HRID 550841 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:14](=O)([O-])[O-].[K+].[K+].[CH3:20][O:21][C:22](=[O:35])[CH:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:23]([C:22]([O:21][CH2:20][CH3:14])=[O:35])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 19796654Methyl 2-bromo-2-[3-(trifluoromethyl)phenyl]acetate

Product 1

HCID 671519624-[Ethoxycarbonyl-(3-trifluoromethyl-phenyl)-methyl]-piperazine-1-carboxylic acid tert-butyl esterYield 74.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Piperazine-1-carboxylic acid tert-butyl ester (1.80 g, 9.68 mmol), potassium carbonate (2.0 g, 14.5 mmole) and Bromo-(3-trifluoromethyl-phenyl)-acetic acid methyl ester (3.0 g, 9.65 mmol) in N,N-dimethylformamide (40 mL) was stirred at room temperature overnight. Concentration gave a crude material which was partitioned between methylene chloride and water. The organic layer was dried over magnesium sulfate and concentrated to give an oil. The crude oil was loaded onto an Isco 120 g column and eluted using 20% ethyl acetate/hexanes to yield 4-[Ethoxycarbonyl-(3-trifluoromethyl-phenyl)-methyl]-piperazine-1-carboxylic acid tert-butyl ester (3.0 g, 74% yield) as a colorless oil. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. concentrationConcentration
  2. customgave a crude material which
  3. customwas partitioned between methylene chloride and water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give an oil
  7. washeluted

Sources & evidence

ORD record
ord-6da0332748724a9e8cbd7cf430ac0c51
Source dataset
uspto-grants-2011_05
Patent number
US07947692B2

Reaction notes

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