3,5-Dimethyl-1-(4-nitrophenyl)piperazine → 4-(3,5-Dimethylpiperazin-1-yl)aniline

HRID 2236573Notes

Reaction equation

HRID 2236573 reaction equation
[CH3:1][CH:2]1[NH:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:3]1>CCO.[Pd]>[CH3:8][CH:6]1[NH:7][CH:2]([CH3:1])[CH2:3][N:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:5]1

Participants

4

Reactant 1

HCID 28296203,5-Dimethyl-1-(4-nitrophenyl)piperazine

Product 1

HCID 176054784-(3,5-Dimethylpiperazin-1-yl)anilineYield 80.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

An amount of 3,5-dimethyl-1-(4-nitrophenyl)piperazine (1.86 g, 7.90 mmol) in EtOH is hydrogenated with Pd/C catalyst for 4 h. The solid is removed by filtration, and solvent is evaporated under vacuum to give pinkish residue. Recrystallization of this residue from MeOH/ether gives 1.30 g (80.2% yield) of pinkish crystal: mp 124-125° C.; MS (ESI) m/z 206.1 (M+H)+1

Workup

  1. customThe solid is removed by filtration, and solvent
  2. customis evaporated under vacuum
  3. customto give pinkish residue
  4. customRecrystallization of this residue from MeOH/ether

Sources & evidence

ORD record
ord-b49a1891c5d4457daba3c49498312fcf
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…