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

HRID 557356Notes

Reaction equation

HRID 557356 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>[Pd].CCO.CO>[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)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

4-Methyl-1-(4-nitrophenyl)piperazine (2.0 g, 9 mmol, Step A) and 10% Pd/C (200 mg) were added to EtOH/MeOH (1:1) (50 ml) at RT. The reaction stirred under a H2 atmosphere (via balloon) overnight. The mixture was filtered through a plug of Celite® and the filtrate was concentrated under reduced pressure to leave the desired material as a light yellow oil. The material was used in subsequent reaction without purification. MS: (ES+) 192 (M+1)+; (ES−): 190 (M−1)−. Calc'd for C11H17N3: 191.14.

Workup

  1. filtrationThe mixture was filtered through a plug of Celite®
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4a3c7eceea774658a18939f7c97a2703
Source dataset
uspto-grants-2011_11
Patent number
US08058445B2

Reaction notes

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