1,4-Dimethyl-3-(4-nitrophenyl)piperazin-2-one → 3-(4-Aminophenyl)-1,4-dimethylpiperazin-2-one

HRID 1968586Notes

Reaction equation

HRID 1968586 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH:4]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[C:3]1=[O:18]>[Pd].C(O)C>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH:4]2[N:5]([CH3:8])[CH2:6][CH2:7][N:2]([CH3:1])[C:3]2=[O:18])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 576250981,4-Dimethyl-3-(4-nitrophenyl)piperazin-2-one

Product 1

HCID 576251203-(4-Aminophenyl)-1,4-dimethylpiperazin-2-oneYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 1j (200 mg, 0.80 mmol), ethanol (5 mL) and 10% palladium on carbon (50% wet, 4 mg dry weight). The reaction flask was purged with hydrogen gas and the reaction mixture stirred under a balloon pressure of hydrogen for 2 h. After this time the flask was purged with nitrogen. The catalyst was removed by filtration through a pad of Celite 521 and the filter cake washed with ethanol (10 mL). The filtrate was concentrated under reduced pressure to afford a 94% yield of 1k (166 mg) as a colorless oil: 1H NMR (500 MHz, DMSO-d6) δ 6.89 (d, 2H, J=8.5 Hz), 6.47 (d, 2H, J=8.5 Hz), 4.94 (s, 2H), 3.53 (td, 1H, J=12.0, 4.0 Hz), 3.44 (m, 1H), 3.21 (dt, 1H, J=12.0, 4.0 Hz), 2.92 (dt, 1H, J=12.0, 4.0 Hz), 2.82 (s, 3H), 2.02 (s, 3H); MS (ESI+) m/z 220 (M+H).

Workup

  1. customA 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. customThe reaction flask was purged with hydrogen gas
  4. customAfter this time the flask was purged with nitrogen
  5. customThe catalyst was removed by filtration through a pad of Celite 521
  6. washthe filter cake washed with ethanol (10 mL)
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5ae5e78330a74901be3ec2f3368b97a2
Source dataset
uspto-grants-2013_04
Patent number
US08426424B2

Reaction notes

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