Potassium Carbonate → 1-[(4-Fluorophenyl)methyl]pyrrolidine-2,5-dione

HRID 853615Notes

Reaction equation

HRID 853615 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1(=[O:13])[NH:11][C:10](=[O:12])[CH2:9][CH2:8]1.[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1>CC(C)=O>[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][N:11]2[C:10](=[O:12])[CH2:9][CH2:8][C:7]2=[O:13])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 11439SuccinimideHCID 680214-Fluorobenzyl bromide

Product 1

HCID 225103401-[(4-Fluorophenyl)methyl]pyrrolidine-2,5-dioneYield 85.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Freshly ground potassium carbonate, K2CO3 (31 g, 225 mmol) was added to dry acetone (200 ml) in a 3-necked flask equipped with drying tube, condenser, and mechanical stirrer. Succinimide (7.43 g, 75 mmol) and 4-fluorobenzylbromide (11.21 mL, 90 mmol) were added. The mixture was refluxed for 19 hours and filtered through Celite. Acetone was removed under vacuum, diluted with EtOAc, washed with saturated aqueous sodium bicarbonate and also with brine, dried (MgSO4), filtered and concentrated to give crude. Crude product was chromatographed (EtOAc/Hexane) on silica gel to give N-4-fluorobenzyl-succinimide 1 as white solid (13.22 g, 85%). 1H NMR (CDCl3) δ 7.4 (dd, 2H), 7.0 (t, 2H), 4.6 (s, 1H), 2.7 (s, 4 H).

Workup

  1. customequipped
  2. customwith drying tube, condenser, and mechanical stirrer
  3. temperatureThe mixture was refluxed for 19 hours
  4. filtrationfiltered through Celite
  5. customAcetone was removed under vacuum
  6. additiondiluted with EtOAc
  7. washwashed with saturated aqueous sodium bicarbonate and also with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give crude
  12. customCrude product was chromatographed (EtOAc/Hexane) on silica gel

Sources & evidence

ORD record
ord-2261eb272a7347afa437919af31d1ef7
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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