p-Fluoronitrobenzene → (2S,5R)-2,5-Dimethyl-1-(4-nitrophenyl)piperazine

HRID 1441358Notes

Reaction equation

HRID 1441358 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][C@@H:15]([CH3:18])[CH2:14][NH:13]1>C(#N)C>[CH3:11][C@H:12]1[CH2:17][NH:16][C@H:15]([CH3:18])[CH2:14][N:13]1[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 2206722,5-Dimethylpiperazine, trans-

Product 1

HCID 57664370(2S,5R)-2,5-Dimethyl-1-(4-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Fluoro-4-nitrobenzene (6 g, 42.52 mmol) and (2R,5S)-2,5-dimethylpiperazine (21.9 g, 191.34 mmol) were heated in acetonitrile (20 ml) at 100° C. for 11 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. Chromatography on silica gel with MeOH: DCM (1:99 to 5:95) gave the title compound as an oil which solidified on standing overnight (8.32 g, 83%). NMR (400 MHz) 1.08 (d, 3H), 1.16 (d, 3H), 2.55 (dd, 1H), 3.18 (m, 2H), 3.34 (m, 2H), 3.95 (m, 1H), 6.91 (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-beb2a42ab81d4e62b9196df9fdd1a5ee
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

Loading…