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

HRID 2236579Notes

Reaction equation

HRID 2236579 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-0024b432a1a840f9ad81b7594b0e0ef3
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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