1-Methyl-4-(4-nitrophenyl)piperidine-2,6-dione → 4-(4-Amino-phenyl)-1-methyl-piperidine-2,6-dione

HRID 2219635Notes

Reaction equation

HRID 2219635 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][CH:5]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:4][C:3]1=[O:18]>CO.[Pd]>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH:5]2[CH2:4][C:3](=[O:18])[N:2]([CH3:1])[C:7](=[O:8])[CH2:6]2)=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 597712961-Methyl-4-(4-nitrophenyl)piperidine-2,6-dione

Product 1

HCID 597711294-(4-Amino-phenyl)-1-methyl-piperidine-2,6-dioneYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 348 mg (1.40 mmol) of 1-methyl-4-(4-nitro-phenyl)-piperidine-2,6-dione (as prepared in the previous step) in MeOH (10 mL) was hydrogenated over 10% Pd/C at 20 psi for 1 h at RT. The mixture was filtered through Celite, the filter cake was washed with MeOH, and the solvents were evaporated in vacuo to afford 289 mg (94%) of the title compound as an off-white solid: Mass spectrum (ESI, m/z): Calcd. for C12H14N2O2, 219.1 (M+H). found 219.1.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter cake was washed with MeOH
  3. customthe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-86124da35bc34daa8fe89b5b3d7b3780
Source dataset
uspto-grants-2008_08
Patent number
US07414050B2

Reaction notes

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