Aniline → 1,5-diphenylpyrrolidin-2-one

HRID 1904618Notes

Reaction equation

HRID 1904618 reaction equation
[C:1]1([CH:7]2[O:12][C:10](=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.NC1C=CC=CC=1>C1C=CC=CC=1>[C:14]1([N:13]2[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH2:9][C:10]2=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8870Benzenamine hydrochloride (1:1)HCID 13884gamma-Phenyl-gamma-butyrolactone

Product 1

HCID 2304381,5-diphenylpyrrolidin-2-oneYield 85.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
180 °C

Procedure

To 20 g of 4-phenyl-γ-butyrolactone were added 28 g of aniline and 7.6 g of aniline hydrochloride, and the mixture was heated with stirring at 180° C. for 5 hours while evaporating the water formed. After cooling, 200 ml of benzene was added, and the mixture was washed with 10% hydrochloric acid and a saturated aqueous sodium chloride solution and dried. After removal of the solvent, the residue was recrystallized from ethyl acetate to give 24.9 g of 1,5-diphenyl-2-pyrrolidone.

Workup

  1. temperaturethe mixture was heated
  2. customwhile evaporating the water
  3. customformed
  4. temperatureAfter cooling
  5. washthe mixture was washed with 10% hydrochloric acid
  6. dry with materiala saturated aqueous sodium chloride solution and dried
  7. customAfter removal of the solvent
  8. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d28b3e090cd74212945bb84ff0f5125b
Source dataset
uspto-grants-1989_06
Patent number
US04839360

Reaction notes

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