N-methyl-N-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide → N-[1-(4-aminophenyl)pyrrolidin-3-yl]-N-methylacetamide

HRID 1354659Notes

Reaction equation

HRID 1354659 reaction equation
[CH3:1][N:2]([CH:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH2:7]1)[C:3](=[O:5])[CH3:4]>C(O)C.C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([N:8]2[CH2:9][CH2:10][CH:6]([N:2]([CH3:1])[C:3](=[O:5])[CH3:4])[CH2:7]2)=[CH:16][CH:15]=1

Participants

5

Reactant 1

HCID 21105631N-methyl-N-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide

Product 1

HCID 21105566N-[1-(4-aminophenyl)pyrrolidin-3-yl]-N-methylacetamide

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of N-methyl-N-[1-(4-nitrophenyl)pyrrolidin-3-yl]acetamide (3.5 g) and palladium(II) hydroxide (20% on carbon; 0.9 g) in ethanol (150 ml) and ethyl acetate (300 ml) was vigorously stirred under a hydrogen atmosphere (atmospheric pressure) for 3 hours. The catalyst was then removed by filtration, and the filtrate was concentrated. This resulted in the product with the molecular weight of 233.32 (C13H19N3O); MS (ESI): 234 (M+H+).

Workup

  1. customThe catalyst was then removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThis resulted in the product with the molecular weight of 233.32 (C13H19N3O)

Sources & evidence

ORD record
ord-4643b8a99a1a4f1c9ddc485ea2d51274
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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