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

HRID 43050

Reaction equation

HRID 43050 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)anilineYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-ethyl-4-(4-nitro-phenyl)-piperazine (Step 1.10) (6.2 g, 26.35 mmol) and Raney nickel (2 g) in MeOH (120 mL) was stirred for 7 h at rt, under a hydrogen atmosphere. The reaction mixture was filtered through a pad of celite and concentrated to afford 5.3 g of the title compound as a violet solid: ESI-MS: 206.1 [M+H]+; TLC: Rf=0.15 (DCM/MeOH+1% NH3aq, 9:1).

Workup

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

Sources & evidence

ORD record
ord-fb5437eac61e4a59b568d9395c71ef5c
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Linked notes

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