1-Methyl-4-(3-nitrobenzyl)piperazine → 3-[(4-Methylpiperazin-1-yl)methyl]aniline

HRID 409660Notes

Reaction equation

HRID 409660 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=2)[CH2:4][CH2:3]1>[Ni].CO>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([NH2:15])[CH:12]=[CH:13][CH:14]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 13771091-Methyl-4-(3-nitrobenzyl)piperazine

Product 1

HCID 64841863-[(4-Methylpiperazin-1-yl)methyl]aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-methyl-4-(3-nitro-benzyl)-piperazine (6.9 g, 29.14 mmol) and Raney Nickel (2 g) in MeOH (150 mL) is stirred for 5 h at RT, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of celite and concentrated to afford the title compound as a yellow solid: ESI-MS: 206.1 [MH]+.

Workup

  1. filtrationThe reaction mixture is filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-30bcfd08325540c2b61922f30ba985b3
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

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