1-Methyl-4-(4-nitrophenyl)piperazine → 4-(4-Methylpiperazin-1-yl)aniline

HRID 2236423Notes

Reaction equation

HRID 2236423 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1>CO.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 28251981-Methyl-4-(4-nitrophenyl)piperazine

Product 1

HCID 7372534-(4-Methylpiperazin-1-yl)anilineYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Methyl-1-(4-nitro-phenyl)-piperazine (1.50 g, 6.78 mmol) is dissolved in MeOH (50 mL), and to this solution is added 10% Pd/C (0.145 g, 6.78 mmol). The reaction mixture is stirred under an atmosphere of H2 for 18 h. The resulting mixture is filtered through celite, and the filtered catalyst is washed with excess EtOAc. The filtrate is concentrated under high vacuum to afford the product as a purple solid (1.28 g, 98%); 1H NMR (DMSO-d6) δ 2.15 (s, 3H), 2.37-2.40 (m, 4H), 2.83-2.87 (m, 4H), 4.48 (s, 2H), 6.43 (d, J=8.8 Hz, 2H), 6.62 (d, J=8.8 Hz, 2H); mass spectrum [(+) ESI], m/z 192 (M+H)+.

Workup

  1. filtrationThe resulting mixture is filtered through celite
  2. washthe filtered catalyst is washed with excess EtOAc
  3. concentrationThe filtrate is concentrated under high vacuum

Sources & evidence

ORD record
ord-758b6c25934b4ad4a18cca651833e38e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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