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

HRID 1280975Notes

Reaction equation

HRID 1280975 reaction equation
[C:1]([CH:4]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[C:6](=O)[CH2:5]1)(O)=[O:2].CCN=C=NCCCN(C)C.C1C=CC2N([OH:38])N=NC=2C=1.[NH3:39]>ClCCl>[C:1]([CH:4]1[CH2:5][CH2:6][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[C:8]1=[O:38])(=[O:2])[NH2:39]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27392001-(4-Chlorobenzyl)-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 184262563-Carbamoyl-1-(4-chlorobenzyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 indioxane (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.

Workup

  1. washwashed with 2N HCl (3 times) and 2 N NaOH aqueous solution (100 mL×4)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-068bc7d1a2eb461cb7be0da80873e2db
Source dataset
uspto-grants-2002_09
Patent number
US06451842B1

Reaction notes

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