1-Acetyl-4-(4-nitrophenyl)piperazine → 1-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-one

HRID 476561

Reaction equation

HRID 476561 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>[Ni].C(O)C>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 28651491-Acetyl-4-(4-nitrophenyl)piperazine

Product 1

HCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A suspension of 4-acetyl-1-(4-nitrophenyl)piperazine [C. A., 67, P101031Z] (30 g, 0.12 mole) and Raney nickel (2.5 g) in ethanol (500 ml) was hydrogenated at 60 psi (414 kPa) and 40° for 6 hours followed by 18 hours at room temperature. The catalyst was subsequently removed by filtration, the solvent removed under reduced pressure and the residue crystallized from ethyl acetate to yield the title compound, m.p. 129°-130° (18.4 g, 71%), which was used directly in the next stage.

Workup

  1. customThe catalyst was subsequently removed by filtration
  2. customthe solvent removed under reduced pressure
  3. customthe residue crystallized from ethyl acetate

Sources & evidence

ORD record
ord-48c587c122724d43b4582d3b03fd9db0
Source dataset
uspto-grants-1989_12
Patent number
US04885294

Linked notes

Loading…