Dimethylformamide → 5-Phenyl-3-{[3-(trifluoromethyl)phenyl]amino}cyclohex-2-en-1-one

HRID 517183Notes

Reaction equation

HRID 517183 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=O)[CH2:10][C:9](=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:15][C:16]([F:25])([F:24])[C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.CN(C)C=O>O.CO>[C:1]1([CH:7]2[CH2:8][C:9](=[O:14])[CH:10]=[C:11]([NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[C:17]([C:16]([F:15])([F:24])[F:25])[CH:18]=3)[CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 73753-(Trifluoromethyl)anilineHCID 5689621,3-Cyclohexanedione, 5-phenyl-HCID 2733225Ytterbium triflate

Product 1

HCID 51584005-Phenyl-3-{[3-(trifluoromethyl)phenyl]amino}cyclohex-2-en-1-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5-phenylcyclohexane-1,3-dione (1.51 g, 8.04 mmol), 3-(trifluoromethyl)-aniline (1.00 mL, 1.29 g, 8.04 mmol), Ytterbium(III) trifluormethanesulfonate (25 mg, 40 μmol, 0.5 mol %) and N,N-dimethylformamide (2.5 mL) is stirred at room temperature over night. Methanol and water are added and the mixture is filtered. The precipitate is dissolved in a mixture of N,N-dimethylformamide, methanol and some drops of aqueous ammonia. Water is added and the precipitate is filtered. Yield: 1.51 g; ESI mass spectrum [M+H]+=332, Retention time HPLC: 1.09 min (Z003—001).

Workup

  1. filtrationthe mixture is filtered
  2. dissolutionThe precipitate is dissolved in a mixture of N,N-dimethylformamide, methanol
  3. additionWater is added
  4. filtrationthe precipitate is filtered
  5. custom1.09 min (Z003—001)

Sources & evidence

ORD record
ord-2e395b4e7da544c8a776981ddf505aaf
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

Loading…