p-Fluoronitrobenzene → 1-Methyl-4-(4-nitrophenyl)piperazine

HRID 2247260Notes

Reaction equation

HRID 2247260 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][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1>>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 531671-Methylpiperazine

Product 1

HCID 28251981-Methyl-4-(4-nitrophenyl)piperazineYield 77.3%

Conditions

Temperature
90 °C

Procedure

1-Fluoro-4-nitrobenzene (3.0 g, 0.021 mol) and 1-methylpiperazine (6.98 ml, 0.63 mol) were combined and heated neat at 90° C. for 48 h. Upon cooling to RT, the resulting brown oil solidified. The crude material was purified by re-crystallization from EtOAc/Hexane mixtures to leave the title compound as an orange solid (3.59 g). MS: (ES+) 222 (M+1)+; (ES−):220 (M−1)−. Calc'd for C11H15N3O2: 221.12.

Workup

  1. temperatureUpon cooling to RT
  2. customThe crude material was purified by re-crystallization from EtOAc/Hexane mixtures

Sources & evidence

ORD record
ord-46a3524c1baa4b1cb6c7f984ce11ae9f
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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