HCID 3522175, compound → 2-(4-Aminophenyl)-1-(4-methylpiperazin-1-yl)ethan-1-one

HRID 2117635Notes

Reaction equation

HRID 2117635 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:19])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH2:4][CH2:3]1.[H][H]>C(O)C.[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)=[O:19])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 3522175HCID 3522175, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 167730792-(4-Aminophenyl)-1-(4-methylpiperazin-1-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-methyl-4-[(4-nitrophenyl)acetyl]piperazine(1.5 g, 5.70 mmol) in ethanol (30 mL) was reduced over palladium/charcoal (10% wt, 50% wet, 150 mg) with hydrogen under atmospheric pressure and room temperature for 18 h. The catalyst was separated by filtration through celite and the solvent evaporated to the title compound as a brown oil. 1H NMR: (400 MHz, CDCl3); 2.21 (2H, t, J 5.01), 2.24 (3H, s), 2.34(2H, t, J 5.13), 3.45 (2H, t, J 5.13), 3.61 (2H, s), 3.63-3.66 (2H, m), 6.64 (2H, d, J 8.56), 7.01 (2H, d, J 8.31).

Workup

  1. customThe catalyst was separated by filtration through celite
  2. customthe solvent evaporated to the title compound as a brown oil

Sources & evidence

ORD record
ord-b60a1465ee7744648aef5ad5bef4f933
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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