Potassium Carbonate → HCID 58901904, compound

HRID 901876Notes

Reaction equation

HRID 901876 reaction equation
F[C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:2]2[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=2[C:4]#[N:5])[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 1456222,3,6-Trifluorobenzonitrile

Product 1

HCID 58901904HCID 58901904, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.0 g (6.36 mmol) of 2,3,6-trifluorobenzonitrile dissolved in 10 mL DMF was added 1.05 g (1.2 eq., 7.63 mmol) potassium carbonate and 1.18 g (1 eq., 6.36 mmol) piperazine-1-carboxylic acid tert-butyl ester. The mixture was stirred 30 minutes to completion, partitioned between ethyl acetate and water, dried over magnesium sulfate and concentrated under reduce d pressure. Column chromatography, eluting with ethyl acetate/hexanes provided 665 mg of 4-(2-cyano-3,6-difluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. washColumn chromatography, eluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2c110fe5864f48519c09712b146f3e01
Source dataset
uspto-grants-2008_04
Patent number
US07365063B2

Reaction notes

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