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

HRID 880485Notes

Reaction equation

HRID 880485 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][C:15]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1)([O-:11])=[O:10].C(N(CC)CC)C>C(#N)C>[CH2:1]([N:21]1[CH2:22][CH2:23][N:18]([C:15]2[CH:14]=[CH:13][C:12]([N+:9]([O-:11])=[O:10])=[CH:17][CH:16]=2)[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 8471TriethylamineHCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 27474271-Benzyl-4-(4-nitrophenyl)piperazineYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl bromide (1.42 mL, 11.6 mmol) was added to a solution of 1-(4-nitrophenyl)piperazine (2.0 g, 11.6 mmol) in acetonitrile (30 mL) with triethylamine (2.68 mL, 19.32 mmol) and refluxed for 12 h. The mixture was concentrated in vacuo and the residue partitioned between water and ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 1-benzyl-4-(4-nitrophenyl)piperazine (2.2 g, 77%).

Workup

  1. temperaturerefluxed for 12 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue partitioned between water and ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fec3168eb7ac417c8b8b5a593c24001b
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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