1-Ethyl-4-(4-nitrophenyl)piperazine → 4-(4-Ethylpiperazin-1-yl)aniline

HRID 409664

Reaction equation

HRID 409664 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]>[Ni].CO>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

4

Reactant 1

HCID 28575491-Ethyl-4-(4-nitrophenyl)piperazine

Product 1

HCID 9367384-(4-Ethylpiperazin-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-ethyl-4-(4-nitro-phenyl)-piperazine (6.2 g, 26.35 mmol) and Raney Nickel (2 g) in MeOH (120 mL) is stirred for 7 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 violet solid: ESI-MS: 206.1 [MH]+; TLC: Rf=0.15 (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-ee549fa061d64d3abbf0f8aeec8dc3b8
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Linked notes

Loading…