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

HRID 228066

Reaction equation

HRID 228066 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)([O-:3])=[O:2].C([O-])([O-])=O.[Na+].[Na+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl.O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:11][CH2:12][N:13]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:14][CH2:15]1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 1009491-(2-Nitrophenyl)piperazine

Product 1

HCID 5181711-Benzyl-4-(2-nitrophenyl)piperazineYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a 500 mL round-bottomed flask equipped with magnetic stirring was added 1-(2-nitrophenyl)piperazine (Emka-Chemie) (30 g, 145 mmol) in CH2Cl2 (300 mL). A solution of Na2CO3 in H2O (61.2 g in 100 mL) was added, and the reaction mixture was stirred for 5 min. Stirring was stopped, benzyl bromide (18.6 mL, 159 mmol) was added, and the reaction was heated at reflux for 4 h. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 (2×50 mL). All organic fractions were combined, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 1-(2-nitrophenyl)-4-benzylpiperazine as an orange oil (42 g). MS (ESI, pos. Ion) m/z: 298 (M+H); MS (ESI, neg. Ion) m/z: 296 (M−H). Calc'd for C17H19N3O2: 297.15.

Workup

  1. customTo a 500 mL round-bottomed flask equipped
  2. stirringthe reaction mixture was stirred for 5 min
  3. stirringStirring
  4. temperaturethe reaction was heated
  5. temperatureat reflux for 4 h
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with CH2Cl2 (2×50 mL)
  8. washwashed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-efef207083b94d27a3d266d02704145a
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Linked notes

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