Triethylamine → 1-(3-Fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-one

HRID 1617391Notes

Reaction equation

HRID 1617391 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[F:8][C:9]1[C:17]([C:18]([F:21])([F:20])[F:19])=[N:16][CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[F:8][C:9]1[C:17]([C:18]([F:21])([F:19])[F:20])=[N:16][CH:15]=[CH:14][C:10]=1[C:11]([N:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1)=[O:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 337214-PiperidoneHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 265964893-Fluoro-2-(trifluoromethyl)isonicotinic acid

Product 1

HCID 584313981-(3-Fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-oneYield 72.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of piperidin-4-one (1 g, 10 mmol) and 3-fluoro-2-(trifluoromethyl)isonicotinic acid (2.32 g, 11.1 mmol) in DMF (20 mL) were added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (5.62 g, 12.7 mmol) and triethylamine (4.43 mL, 31.8 mmol). The mixture was stirred at room temperature overnight and diluted with EtOAc. The solution was washed with brine, dried with sodium sulfate, filtered and concentrated. Purification on silica gel with 50-100% EtOAc/hexanes gave 2.1 g (70% yield) of the title compound. LC/MS found: 291.2 (M+1)+.

Workup

  1. washThe solution was washed with brine
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification on silica gel with 50-100% EtOAc/hexanes

Sources & evidence

ORD record
ord-241777ae01e844a589dd21892e000513
Source dataset
uspto-grants-2014_07
Patent number
US08765734B2

Reaction notes

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