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

HRID 39676
Notes
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Reaction equation

HRID 39676 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 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-3b53355216574a55960b7b5cb5f073e3
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524738B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes