Piperazine → 1-(2-fluoro-4-nitrophenyl)piperazine

HRID 2364838Notes

Reaction equation

HRID 2364838 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[F:17]>CS(C)=O.CCOC(C)=O>[F:17][C:9]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=1[N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 4837PiperazineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 27830661-(2-fluoro-4-nitrophenyl)piperazineYield 100%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a warm solution of piperazine (7.78 g, 90 mmol) in DMSO (40 mL) was added dropwise 1,2-difluoro-4-nitrobenzene (2.0 mL, 18.07 mmol). The solution was stirred at 70° C. for 2 h, cooled to room temperature, diluted with EtOAc, washed with H2O, brine, dried (Na2SO4), filtered and solvent removed in vacuo to give the title compound (4.05 g, 17.98 mmol, 100%). 1H NMR (400 MHz, CDCl3) δ ppm 3.03-3.09 (m, 4H) 3.26-3.29 (m, 4H) 6.91 (t, J=8.8 Hz, 1H) 7.91 (dd, J=13.1, 2.6 Hz, 1H) 7.96-8.01 (m, 1H). MS (ESI) m/z 226 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with H2O, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-6d5d70e1634b491a87a6353ca57f679a
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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