1-Ethyl-4-(4-nitrobenzyl)piperazine → 4-[(4-Ethylpiperazin-1-yl)methyl]aniline

HRID 1038719Notes

Reaction equation

HRID 1038719 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH2:5][CH2:4]1)[CH3:2]>[Ni].CO>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 7925571-Ethyl-4-(4-nitrobenzyl)piperazine

Product 1

HCID 10849964-[(4-Ethylpiperazin-1-yl)methyl]anilineYield 98.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-ethyl-4-(4-nitro-benzyl)-piperazine (7.2 g, 29.14 mmol) and Raney Nickel (1.5 g) in MeOH (100 mL) is stirred for 6 h at RT, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of celite and concentrated to afford 6.3 g of the title compound as a yellow solid: ESI-MS: 220.1 [MH]+; TLC: Rf=0.08 (DCM/MeOH+1% NH3aq, 9:1).

Workup

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

Sources & evidence

ORD record
ord-c7699ef0cdbe4ad5ada378418fe2b3c0
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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