Aniline → 3-Anilino-1-benzylpyrrolidine

HRID 992271Notes

Reaction equation

HRID 992271 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>>[NH:24]([CH:10]1[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 156236681-Benzylpyrrolidin-3-yl 4-methylbenzenesulfonate

Product 1

HCID 111843263-Anilino-1-benzylpyrrolidineYield 47.8%

Conditions

Temperature
160 °C

Procedure

1-Benzyl-3-(p-toluenesulfonyloxy)pyrrolidine (3.3 g) and aniline (1.3 g) were mixed and stirred under heating at 160° C. for 3 hours. After the completion of the reaction, the mixture was cooled to room temperature, and an aqueous potassium carbonate solution was added thereto. The obtained mixture was extracted with chloroform, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (chloroform:methanol=40:1). The obtained eluate was concentrated to give 3-anilino-1-benzylpyrrolidine (1.2 g).

Workup

  1. customAfter the completion of the reaction
  2. temperaturethe mixture was cooled to room temperature
  3. extractionThe obtained mixture was extracted with chloroform
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe obtained eluate was concentrated

Sources & evidence

ORD record
ord-26282bd65f6e48e1abfb7d157cebbfa4
Source dataset
uspto-grants-2002_10
Patent number
US06468998B1

Reaction notes

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