Potassium Carbonate → 1-(2-Fluoro-4-nitrophenyl)-4-methylpiperazine

HRID 1398074Notes

Reaction equation

HRID 1398074 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:16]1[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 27830541-(2-Fluoro-4-nitrophenyl)-4-methylpiperazineYield 68.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3.9 mL (35 mmol) of 3,4-difluoronitrobenzene in 60 mL of dimethyl sulfoxide were added 9.7 mL (87.5 mmol) of N-methylpiperazine and 12.1 g (87.5 mmol) of potassium carbonate, and the mixture was refluxed for 5 hours at 100° C. The reaction mixture was cooled to room temperature and poured into 500 mL of ice water, and the resulting precipitates were collected. The collected precipitates were dissolved in 2M-HCl aqueous solution and washed with ether. The aqueous layer was neutralized with 4M-NaOH aqueous solution to give the precipitates. The precipitates were collected to give 5.71 g (68%) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe resulting precipitates
  3. customwere collected
  4. customThe collected precipitates
  5. dissolutionwere dissolved in 2M-HCl aqueous solution
  6. washwashed with ether
  7. customto give the precipitates
  8. customThe precipitates were collected

Sources & evidence

ORD record
ord-49f02b89b92745039e6127354bb52499
Source dataset
uspto-grants-2014_12
Patent number
US08901315B2

Reaction notes

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