4-(4-Nitrophenyl)piperidine-2,6-dione → 4-(4-Aminophenyl)piperidine-2,6-dione

HRID 1008879Notes

Reaction equation

HRID 1008879 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][C:14](=[O:16])[NH:13][C:12](=[O:17])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:11][C:12](=[O:17])[NH:13][C:14](=[O:16])[CH2:15]2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 534263034-(4-Nitrophenyl)piperidine-2,6-dione

Product 1

HCID 597711544-(4-Aminophenyl)piperidine-2,6-dioneYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 197 mg (0.841 mmol) of 4-(4-nitro-phenyl)-piperidine-2,6-dione (as prepared in the previous step) in methyl alcohol (MeOH) (15 mL) was hydrogenated over 10% Pd/C at 20 psi for 5 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 106 mg (62%) of the title compound as an off-white solid: Mass spectrum (ESI, m/z): Calcd. for C11H12N2O2, 205.1 (M+H). found 205.1.

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-8f871ad3d41945718d3032b5fa36b504
Source dataset
uspto-grants-2011_07
Patent number
US07973035B2

Reaction notes

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