p-Fluoronitrobenzene → 1-Ethyl-4-(4-nitrophenyl)piperazine

HRID 1915655Notes

Reaction equation

HRID 1915655 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[CH3:12].C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH2:11]([N:13]1[CH2:18][CH2:17][N:16]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:15][CH2:14]1)[CH3:12]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 791961-EthylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 28575491-Ethyl-4-(4-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 4-fluoro-1-nitrobenzene (1 eq) in N,N-dimethylformamide was added Ethyl piperazine (2 eq) and N,N-diisopropylethyl amine (2 eq) and heated at 80° C. for 16 h. Concentrated the resultant mixture and partitioned between ethyl acetate and water. The organic layer was then washed with brine and dried with sodium sulfate and concentrated. Passed through a plug of silica to yield 4-Ethyl-1-(4-nitrophenyl)piperazine. MS: MH+=235.

Workup

  1. concentrationConcentrated the resultant mixture
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was then washed with brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2bc88bac22004d68ac3fa83149d7c415
Source dataset
uspto-grants-2013_12
Patent number
US08614330B2

Reaction notes

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