Benzyl Chloride → 1-Benzyl-3-pyrrolidinone

HRID 338830Notes

Reaction equation

HRID 338830 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3]1.C(OCC)(=O)C.[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCCl.C(Cl)Cl.O>[CH2:14]([N:2]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 7503Benzyl ChlorideHCID 8857Ethyl AcetateHCID 19106857Pyrrolidin-3-one hydrochloride

Product 1

HCID 698901-Benzyl-3-pyrrolidinoneYield 93.9%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of pyrrolidin-3-one hydrochloride (7.40 g, 60.9 mmol) in DCE (122 mL) was added ethyl acetate (23.9 mL, 137 mmol) followed by benzyl chloride (8.63 g, 68.2 mmol) at ambient temperature. The reaction was heated to 70° C. for 2 hours. The reaction was cooled, diluted with DCM (100 mL), water (100 mL), the layers were separated, and the organic layer was dried (MgSO4), filtered and concentrated under reduced pressure to give 1-benzylpyrrolidin-3-one (10.01 g, 57.2 mmol, 93.9% yield).

Workup

  1. temperatureThe reaction was cooled
  2. customthe layers were separated
  3. dry with materialthe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4071ed4e6bc34e8193a28e2501ac941f
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

Loading…