Water → 1-(Phenylmethyl)-2,5-pyrrolidinedione

HRID 2367228

Reaction equation

HRID 2367228 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C:2]1=[O:7].C([O-])([O-])=O.[K+].[K+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C=O)C>[C:15]1([CH2:14][N:1]2[C:5](=[O:6])[CH2:4][CH2:3][C:2]2=[O:7])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11439Succinimide

Product 1

HCID 952411-(Phenylmethyl)-2,5-pyrrolidinedioneYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To 2,5-pyrrolidinedione (2.5 g, 25.2 mmol) in DMF (50 mL) was added K2CO3 (4.18 g, 30.3 mmol) followed by benzyl bromide (3.00 mL, 25.2 mmol), and the reaction mixture was stirred overnight at 55° C. Water was added to the reaction mixture (˜200 mL) and a precipitate was immediately observed. The precipitate was filtered, and the white solid was washed with water and dried to afford the title compound (2.7 g, 57%). 1H NMR (400 MHz, CDCl3): δ 2.73 (s, 4H), 4.68 (s, 2H), 7.28-7.37 (m, 3H), 7.39-7.44 (m, 2H).

Workup

  1. filtrationThe precipitate was filtered
  2. washthe white solid was washed with water
  3. customdried

Sources & evidence

ORD record
ord-bc43a7dcc6a04a6dafef526f54040f81
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Linked notes

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