1-(3-Chloro-4-nitro-phenyl)-4-ethyl-piperazine → 2-Chloro-4-(4-ethyl-piperazin-1-yl)-phenylamine

HRID 409691

Reaction equation

HRID 409691 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH3:18])[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>[Ni].CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH3:18])[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 1

HCID 691619981-(3-Chloro-4-nitro-phenyl)-4-ethyl-piperazine

Product 1

HCID 692533582-Chloro-4-(4-ethyl-piperazin-1-yl)-phenylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-(3-chloro-4-nitro-phenyl)-4-ethyl-piperazine (1 g, 3.7 mmol) and Raney Nickel (0.1 g) in MeOH (20 mL) is stirred for 8 h at RT, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of celite and concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 95:5) to afford the title compound as an off-white solid: ESI-MS: 240.1/242.1 [MH]+; tR=0.90 min (system 1); TLC: Rf=0.46 (DCM/MeOH+1% NH3aq, 95:5).

Workup

  1. filtrationThe reaction mixture is filtered through a pad of celite
  2. concentrationconcentrated
  3. customThe residue is purified by silica gel column chromatography (DCM/MeOH+1% NH3aq, 95:5)

Sources & evidence

ORD record
ord-9c08feec7d764f4fafa138602614a059
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Linked notes

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