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

HRID 1262235Notes

Reaction equation

HRID 1262235 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]>C(O)C.[Pd]>[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 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1,4-Dimethyl-3-(4-nitro-phenyl)-piperazin-2-one (445 mg, 1.78 mmol) was dissolved in ethanol (11 mL) and 10% Palladium on Carbon (50% Wet) (19.0 mg, 0.00893 mmol) was added. The reaction was hydrogenated at 50 psi. overnight and then filtered through celite to remove the catalyst. The reaction was then concentrated under reduced pressure to obtain 3-(4-amino-phenyl)-1,4-dimethyl-piperazin-2-one as a yellow foam (391 mg, 100%). LCMS (m/e) 220 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 7.12 (d, 2H, J=8.2 Hz), 6.64 (d, 2H, J=8.2 Hz), 3.76-3.66 (m, 1H), 3.68 (s, 1H), 3.26-3.18 (m, 1H), 3.05-2.97 (m, 1H), 2.97 (s, 3H), 2.71-2.61 (m, 1H), 2.19 (s, 3H).

Workup

  1. filtrationovernight and then filtered through celite
  2. customto remove the catalyst
  3. concentrationThe reaction was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-5aeadfdeacff449d807eb30fc06bae0b
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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