Hydrazine hydrate (1:1) → N-phenylpyrrolidin-3-amine

HRID 992272Notes

Reaction equation

HRID 992272 reaction equation
[NH:1]([CH:8]1[CH2:12][CH2:11][N:10](CC2C=CC=CC=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C.[C].[Pd]>[NH:1]([CH:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 111843263-Anilino-1-benzylpyrrolidine

Product 1

HCID 11412557N-phenylpyrrolidin-3-amineYield 86.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

3-Anilino-1-benzylpyrrolidine (1.2 g) was dissolved in ethanol (20 ml), 10% palladium-carbon (0.5 g) was added thereto. The mixture was stirred at room temperature, and hydrazine monohydrate (0.24 g) was added. The mixture was stirred under heating for 2 hours and cooled to room temperature. 10% Palladium-carbon was filtered off with celite, and the filtrate was concentrated to give 3-anilinopyrrolidine (0.67 g).

Workup

  1. stirringThe mixture was stirred
  2. temperatureunder heating for 2 hours
  3. temperaturecooled to room temperature
  4. filtration10% Palladium-carbon was filtered off with celite
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-084b726945294eec873450433aff0e5c
Source dataset
uspto-grants-2002_10
Patent number
US06468998B1

Reaction notes

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