Ammonia → 3-Carbamoyl-1-(4-chlorobenzyl)pyrrolidin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1-(4-Chlorobenzyl)-5-oxopyrrolidine-3-carboxylic acid	HCID 2739200	—
Solvent	Dichloromethane	HCID 6344	—
Product	3-Carbamoyl-1-(4-chlorobenzyl)pyrrolidin-2-one	HCID 18426256	—

Reaction Steps

To a mixture of 4-carboxy-1-(4-chlorobenzyl)pyrrolidin-2-one (5.05 g, 20 mmol), EDCI (2.85 g, 22 mmol), HOBt (2.97 g, 22 mmol) and dichloromethane (100 mL) was added 0.5 M ammonia in dioxane (60 mL, 30 mmol). The reaction mixture was stirred at room temperature for 15 h and washed with 2N HCl (3 times) and 2 N NaOH aqueous solution (100 mL×4). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to afford 3-carbamoyl-1-(4-chlorobenzyl)pyrrolidin-2-one (1.49 g) as a colorless solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06362177B1
Source dataset	uspto-grants-2002_03
ORD ID	ord-4114cb5c40d8455699bb32721044f93c
Source note	uspto-grants-2002_03