Water → 1-(3-Bromo-4-nitrophenyl)-4-methylpiperazine

HRID 1445176Notes

Reaction equation

HRID 1445176 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.O>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([N:16]2[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]2)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 531671-MethylpiperazineHCID 27569932-Bromo-4-fluoro-1-nitrobenzene

Product 1

HCID 117815411-(3-Bromo-4-nitrophenyl)-4-methylpiperazineYield 45%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-4-fluoronitrobenzene (949 mg, 4.31 mmol) was added in two portions to neat N-methypiperazine (8 mL) at 0° C. and allowed to warm to room temperature. The reaction was heated to 60° C. for 1 h, and then it was diluted with 50 mL of EtOAc and poured into H2O (50 mL). The layers were separated and the organic layer was washed with satd aq NaHCO3, dried (Na2SO4), and concentrated in vacuo to afford 580 mg (45%) of the title compound as a yellow solid: Mass spectrum (ESI, m/z): Calcd. for C11H14BrN3O2, 300.0 (M+H), found 300.1.

Workup

  1. temperatureThe reaction was heated to 60° C. for 1 h
  2. customThe layers were separated
  3. washthe organic layer was washed with satd aq NaHCO3
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8fe2f52e40143c085dd255a27447b39
Source dataset
uspto-grants-2010_02
Patent number
US07662837B2

Reaction notes

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