1-[(4-Nitrophenyl)acetyl]pyrrolidine → 2-(4-Aminophenyl)-1-(pyrrolidin-1-yl)ethan-1-one

HRID 546645Notes

Reaction equation

HRID 546645 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:6][CH:5]=1)([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[O:12]=[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:10][C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 13777051-[(4-Nitrophenyl)acetyl]pyrrolidineHCID 2723923Ammonium formate

Product 1

HCID 167707122-(4-Aminophenyl)-1-(pyrrolidin-1-yl)ethan-1-oneYield 70.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 0.8 g of 1-[(4-nitrophenyl)acetyl]pyrrolidine obtained in stage a) below in 20 mL of methanol are added, under argon, 1.72 g of ammonium formate and 36 mg of 10% palladium-on-charcoal. The reaction mixture is stirred at room temperature for 1 hour and then filtered through Celite and concentrated under reduced pressure. The residue is taken up in water and extracted with dichloromethane. The organic phase is then washed with water and with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure to give 0.49 g of 4-(2-oxo-2-pyrrolidin-1-ylethyl)aniline, the characteristics of which are as follows:

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with dichloromethane
  4. washThe organic phase is then washed with water and with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-29c815ab8eda4735b5f00f665d91f144
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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