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

HRID 1441357Notes

Reaction equation

HRID 1441357 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][C@@H:12]1[CH2:17][NH:16][CH2:15][C@H:14]([CH3:18])[NH:13]1>C(#N)C>[CH3:11][C@H:12]1[NH:13][C@@H:14]([CH3:18])[CH2:15][N:16]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:17]1

Participants

4

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Product 1

HCID 7059963cis-3,5-Dimethyl-1-(4-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Fluoro-4-nitrobenzene (10 g, 70.87 mmol) and (2R,6S)-2,6-dimethylpiperazine (17 g, 148.83 mmol) were heated in acetonitrile (25 ml) at 70° C. for 2 h. The solution was concentrated in vacuo, then the residue was partitioned between DCM and water+sat. sodium hydrogen carbonate. The organic extract was washed with water (4 times), brine, dried and concentrated to give the title compound as a yellow solid which was dried in vac oven overnight at 50° C. (16.13 g, 97%). NMR (400 MHz) 1.04 (d, 6H), 2.39 (m, 2H), 2.77 (m, 2H), 3.89 (dd, 2H), 7.02 (d, 2H), 8.03 (d, 2H); m/z 236.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was partitioned between DCM and water+
  3. extractionThe organic extract
  4. washwas washed with water (4 times), brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fdd4de04117d4a8bb563412c2eecf870
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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