Potassium Carbonate → HCID 2947839, compound

HRID 2066713Notes

Reaction equation

HRID 2066713 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-cd7e300c79f547f3b34d7bc194656ef1
Source dataset
uspto-grants-2012_10
Patent number
US08293746B2

Reaction notes

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