Benzyl Bromide → 1-Benzyl-4-(2-nitrophenyl)piperazine

HRID 1419581Notes

Reaction equation

HRID 1419581 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([N:21]1[CH2:22][CH2:23][N:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N+:9]([O-:11])=[O:10])[CH2:19][CH2:20]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1009491-(2-Nitrophenyl)piperazine

Product 1

HCID 5181711-Benzyl-4-(2-nitrophenyl)piperazineYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (3.1 mL, 26 mmol) was added to a mixture of 1-(2-nitrophenyl)piperazine (4.91 g, 24 mmol) and potassium carbonate (8.2 g, 59 mmol) in dimethylformamide (30 mL) and the mixture was stirred at room temperature for 2 h. The solvent was evaporated under reduced pressure and the residue was azeotroped with xylene. The residue was diluted with ethyl acetate, washed with brine (×3), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/Hexane (60:40) to give the title compound as an orange oil (4.0 g, 57%). δH (250 MHz, CDCl3) 7.75 (1H, dd, J 1.6, 8.1 Hz), 7.46 (1H, dt, J 1.6, 7.3 Hz), 7.34-7.24 (5H, m), 7.12 (1H, dd, J 7.1, 8.3 Hz), 7.01 (1H, dt, J 1.2, 8.3 Hz), 3.57 (2H, s), 3.10-3.05 (4H, m), and 2.63-2.58 (4H, m).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was azeotroped with xylene
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with brine (×3)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluting with EtOAc/Hexane (60:40)

Sources & evidence

ORD record
ord-912fc5ab4b654e938383501cb13c4596
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

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