Potassium Carbonate → 1-Ethyl-4-(3-fluoro-4-nitro-phenyl)-piperazine

HRID 2066724Notes

Reaction equation

HRID 2066724 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].[F:9][C:10]1[CH:15]=[C:14](F)[CH:13]=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:14]2[CH:13]=[CH:12][C:11]([N+:17]([O-:19])=[O:18])=[C:10]([F:9])[CH:15]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 679672,4-DifluoronitrobenzeneHCID 791961-Ethylpiperazine

Product 1

HCID 691789001-Ethyl-4-(3-fluoro-4-nitro-phenyl)-piperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

N-Ethylpiperazine (4.8 mL, 37.7 mmol, 1.2 equiv) is added to a mixture of 2,4-difluoronitrobenzene (5 g, 31.4 mmol) and potassium carbonate (8.7 g, 62.9 mmol, 2 equiv) in DMF (50 mL). The reaction mixture is stirred at 100° C. for 6 h, allowed to cool to RT, diluted with H2O and extracted with EtOAc. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 95:5) to provide the title compound as a yellow oil: ES-MS: 254.1 [MH]+; TLC: Rf=0.67 (DCM/MeOH+1% NH3aq, 95:5).

Workup

  1. temperatureto cool to RT
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 95:5)

Sources & evidence

ORD record
ord-dc860d0b392f495ab5cba059abfe2465
Source dataset
uspto-grants-2012_10
Patent number
US08293746B2

Reaction notes

Loading…