Potassium Carbonate → HCID 2947839, compound

HRID 409683Notes

Reaction equation

HRID 409683 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:11]=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:14][C:15]=1F.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:15]2[CH:14]=[CH:13][C:12]([N+:17]([O-:19])=[O:18])=[CH:11][C:10]=2[F:9])[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 2947839HCID 2947839, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

N-Ethylpiperazine (0.96 mL, 7.6 mmol, 1.2 equiv) is added to a mixture of 3,4-difluoronitrobenzene (0.7 mL, 6.32 mmol) and potassium carbonate (1.74 g, 12.6 mmol, 2 equiv) in DMF (10 mL). The reaction mixture is stirred at 90° C. for 17 h, allowed to cool to RT, diluted with H2O and extracted with DCM. 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, 97:3) to provide the title compound as a yellow solid: ES-MS: 254.1 [MH]+; tR=2.65 min (system 1); Rf=0.30 (DCM/MeOH+1% NH3aq, 93:7).

Workup

  1. temperatureto cool to RT
  2. extractionextracted with DCM
  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, 97:3)

Sources & evidence

ORD record
ord-442a0551c1c241889e66912d9fb02e3d
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

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