1-Methylpiperazine → 1-(2-Fluoro-4-nitrophenyl)-4-methylpiperazine

HRID 10774

Reaction equation

HRID 10774 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(#N)C>[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

4

Reactant 2

HCID 531671-MethylpiperazineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 27830541-(2-Fluoro-4-nitrophenyl)-4-methylpiperazineYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3,4-difluoronitrobenzene (12.00 g, 75.4 mmol) (Aldrich) and N-methylpiperazine (18.89 g, 188.6 mmol) in acetonitrile (150 mL) was heated at reflux for 3 h. The reaction mixture was allowed to stand overnight at room temperature, then the solvent was evaporated under reduced pressure and the residue was partitioned between water and ethyl acetate (200 mL each). The aqueous layer was extracted with ethyl acetate (3×200 mL) and the combined organic layers were then washed with water and brine (200 mL each), dried (MgSO4), filtered, and evaporated under reduced pressure to give 1-(2-fluoro-4-nitrophenyl)-4-methylpiperazine as a pale brown solid (17.5 g, 97%, mp 68–70° C.).

Workup

  1. temperatureat reflux for 3 h
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between water and ethyl acetate (200 mL each)
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×200 mL)
  5. washthe combined organic layers were then washed with water and brine (200 mL each)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7fc712df9bea40238aa90ddb61a7176d
Source dataset
uspto-grants-2006_08
Patent number
US07094896B2

Linked notes

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