p-Fluoronitrobenzene → 3,5-Dimethyl-1-(4-nitrophenyl)piperazine

HRID 2236572Notes

Reaction equation

HRID 2236572 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:11][CH:12]1[CH2:17][NH:16][CH2:15][CH:14]([CH3:18])[NH:13]1>C(#N)C>[CH3:11][CH:12]1[NH:13][CH:14]([CH3:18])[CH2:15][N:16]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:17]1

Participants

4

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 660562,6-Dimethylpiperazine

Product 1

HCID 28296203,5-Dimethyl-1-(4-nitrophenyl)piperazineYield 89.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An amount 4-nitrophenylfluoride (2.0 mL, 18.85 mmol) in 20 mL of acetonitrile is added 2,6-dimethylpiperazine (2.58 g, 22.62 mmol). The reaction mixture is reflux under N2 overnight. Mass spectroscopy suggested the completion of reaction. Solvent is subsequently evaporated under vacuum. The collected yellow solid is dissolved in chloroform and washed twice with 200 mL of saturated NaHCO3 solution, and once with 100 mL of brine. The organic portion is dried over Mg2SO4, filtered, evaporated to give yellow solid which is re-crystallized from EtOAc/Hexane to give 3.98 g (89.8% yield) of bright yellow crystals: mp 124-125° C.; MS (ESI) m/z 236.1 (M+H)+1

Workup

  1. temperatureThe reaction mixture is reflux under N2 overnight
  2. customthe completion of reaction
  3. customSolvent is subsequently evaporated under vacuum
  4. dissolutionThe collected yellow solid is dissolved in chloroform
  5. washwashed twice with 200 mL of saturated NaHCO3 solution
  6. dry with materialThe organic portion is dried over Mg2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give yellow solid which
  10. customis re-crystallized from EtOAc/Hexane

Sources & evidence

ORD record
ord-d255a287b40d407286b89efae6452dd0
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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