1-(4-(3-Methoxy-4-nitrophenyl)piperazin-1-yl)ethanone → 1-(4-(4-aMino-3-Methoxyphenyl)piperazin-1-yl)ethanone

HRID 1014211Notes

Reaction equation

HRID 1014211 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)=[C:12]([O:19][CH3:20])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>C(O)C.C(OCC)(=O)C.[Pd].[C]>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([O:19][CH3:20])[CH:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 594418231-(4-(3-Methoxy-4-nitrophenyl)piperazin-1-yl)ethanone

Product 1

HCID 552327371-(4-(4-aMino-3-Methoxyphenyl)piperazin-1-yl)ethanoneYield 84.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 1-acetyl-4-[3-(methyloxy)-4-nitrophenyl]piperazine (0.4 g, 1.43 mmol) in ethanol: ethyl acetate (5:1) was added 10% Pd/carbon (˜0.100 g, Lancaster) and the mixture was rapidly stirred under 50 psi H2 overnight. The catalyst was removed by vacuum filtration through a celite pad, rinsed with methanol, and concentrated by rotary evaporation to give 4-(4-acetyl-1-piperazinyl)-2-(methyloxy)aniline (0.3 g, 84%). ESIMS (M+H)+=250.

Workup

  1. customThe catalyst was removed by vacuum filtration through a celite pad
  2. washrinsed with methanol
  3. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-6705cb491a0c489f915ce0c7ae3e1127
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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