Methanol → 1-(3-Aminophenyl)-4-methylpiperazin-2-one

HRID 1864052Notes

Reaction equation

HRID 1864052 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)[CH2:4][CH2:3]1.C[OH:18]>O.[Pd]>[NH2:14][C:10]1[CH:9]=[C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][C:4]2=[O:18])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 121521611-Methyl-4-(3-nitrophenyl)piperazine

Product 1

HCID 579741721-(3-Aminophenyl)-4-methylpiperazin-2-oneYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Pd/C (10%, 420 mg) was added to a solution of 1-methyl-4-(3-nitrophenyl)piperazine (8.4 g) in methanol (500 mL) and water (20 mL). The reaction mixture was stirred and degassed with nitrogen, and the vessel was charged with H2 gas at atmospheric pressure. The reaction was allowed to proceed overnight after which time the Pd/C was removed by filtration over celite and the methanol and water were removed in vacuo to give 1-(3-aminophenyl)-4-methyl-2-piperazinone as a yellow solid (7.08 g, 95% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.07 (1H, t, J=7.83 Hz) 6.48-6.55 (2H, m) 6.46 (1H, d, J=1.01 Hz) 6.44 (1H, s) 3.88 (4H, s) 3.54 (2H, br. s.) 2.82 (3H, s)

Workup

  1. customdegassed with nitrogen
  2. additionthe vessel was charged with H2 gas at atmospheric pressure
  3. customafter which time the Pd/C was removed by filtration over celite
  4. customthe methanol and water were removed in vacuo

Sources & evidence

ORD record
ord-875e0ca22be846319cffc7f73e2a94fd
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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