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

HRID 450049Notes

Reaction equation

HRID 450049 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.ClCCl.[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

5

Reactant 1

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

Product 1

HCID 7372534-(4-Methylpiperazin-1-yl)anilineYield 64%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1-Methyl-4-(4-nitro-phenyl)-piperazine (200 mg) was hydrogenated over 10% Pd—C (20 mg) in methanol (20 ml) at atmospheric pressure until no further gas uptake was observed. The reaction mixture was then filtered over celite and concentrated to give a crude solid. Column chromatography over silica gel using 4% methanol in dichloromethane gave 4-(4-methyl-piperazin-1-yl)-phenylamine (110 mg, 64%) as solid.

Workup

  1. filtrationThe reaction mixture was then filtered over celite and
  2. concentrationconcentrated
  3. customto give a crude solid

Sources & evidence

ORD record
ord-b11ab8e1ca1c4c78bc469e04ed40f638
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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