Dimethylformamide → N-Pyridin-2-yl-N~2~-[1-(trifluoroacetyl)piperidin-4-yl]glycinamide

HRID 2193048Notes

Reaction equation

HRID 2193048 reaction equation
CN(C)C=O.Cl.[F:7][C:8]([F:19])([F:18])[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][CH2:12]1)=[O:10].Br[CH2:21][C:22]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)=[O:23].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[N:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[NH:24][C:22](=[O:23])[CH2:21][NH:17][CH:14]1[CH2:15][CH2:16][N:11]([C:9](=[O:10])[C:8]([F:7])([F:18])[F:19])[CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 34158372-bromo-N-pyridin-2-yl-acetamideHCID 866331901-(4-Aminopiperidin-1-YL)-2,2,2-trifluoroethan-1-one hydrochloride

Product 1

HCID 59398027N-Pyridin-2-yl-N~2~-[1-(trifluoroacetyl)piperidin-4-yl]glycinamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 15 mL of an N,N-dimethylformamide solution containing 1.5 g of 1-(trifluoroacetyl)piperidine-4-amine hydrochloride, 1.4 g of 2-bromo-N-(pyridin-2-yl)acetamide and 1.8 g of potassium carbonate were added, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was added with ethyl acetate and water. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed sequentially with water and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=10:1] to obtain 1.1 g of a light brown oily substance, N-(pyridin-2-yl)-N2-(1-(trifluoroacetyl)piperidin-4-yl)glycinamide.

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe resultant solution was washed sequentially with water
  5. dry with materialan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=10:1]

Sources & evidence

ORD record
ord-6f94c368614d4dfca23aa6b35ab55a2f
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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