Potassium Carbonate → 3-Anilino-1-(2-(4-fluorophenyl)ethyl)pyrrolidine

HRID 992273Notes

Reaction equation

HRID 992273 reaction equation
[NH:1]([CH:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH:1]([CH:8]1[CH2:12][CH2:11][N:10]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11412557N-phenylpyrrolidin-3-amineHCID 17390106Benzeneethanol, 4-fluoro-, 1-(4-methylbenzenesulfonate)

Product 1

HCID 184119313-Anilino-1-(2-(4-fluorophenyl)ethyl)pyrrolidineYield 71.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Anilinopyrrolidine (0.67 g) and 2-(4-fluorophenyl)ethyl p-toluenesulfonate (1.2 g) were dissolved in acetonitrile (20 ml), and potassium carbonate (2 g) was added. The mixture was refluxed for 3 hours, and after the completion of the reaction, the solvent was evaporated under reduced pressure. The obtained residue was dissolved in ethyl acetate, washed with an aqueous potassium carbonate solution, 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=20:1). The obtained eluate was concentrated to give 3-anilino-1-(2-(4-fluorophenyl)ethyl)pyrrolidine (0.83 g).

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customafter the completion of the reaction
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe obtained residue was dissolved in ethyl acetate
  5. washwashed with an aqueous potassium carbonate solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. concentrationThe obtained eluate was concentrated

Sources & evidence

ORD record
ord-b476d6be0df248f4a61efa65bb7dea27
Source dataset
uspto-grants-2002_10
Patent number
US06468998B1

Reaction notes

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