1-Ethyl-4-(3-fluoro-4-nitro-phenyl)-piperazine → 4-(4-Ethylpiperazin-1-yl)-2-fluoroaniline

HRID 409693Notes

Reaction equation

HRID 409693 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)=[C:11]([F:18])[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]>CO.[Pd]>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([F:18])[CH:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

4

Reactant 1

HCID 691789001-Ethyl-4-(3-fluoro-4-nitro-phenyl)-piperazine

Product 1

HCID 450955104-(4-Ethylpiperazin-1-yl)-2-fluoroaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-ethyl-4-(3-fluoro-4-nitro-phenyl)-piperazine (7 g, 27.7 mmol) and Pd (10%) on carbon (0.35 g) in MeOH (140 mL) is stirred for 3 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 a white solid: ESI-MS: 224.1 [MH]+; TLC: Rf=0.54 (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-c0b88ee6db124317b89410935711c985
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

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