1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-Carbamoyl-1-(4-chlorobenzyl)pyrrolidin-2-one

HRID 2187793Notes

Reaction equation

HRID 2187793 reaction equation
C([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(=O)C1)(O)=O.CCN=C=NCCC[N:26]([CH3:28])C.C1C=CC2N([OH:38])N=NC=2C=1.[O:39]1[CH2:44][CH2:43]OCC1>ClCCl>[C:28]([CH:43]1[CH2:4][CH2:8][N:7]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[C:44]1=[O:39])(=[O:38])[NH2:26]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 312751,4-DioxaneHCID 757711-HydroxybenzotriazoleHCID 27392001-(4-Chlorobenzyl)-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 184262563-Carbamoyl-1-(4-chlorobenzyl)pyrrolidin-2-oneYield 29.5%

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 Mammonia in dioxane (60 mL, 30 mmol). The reaction mixture was stirred at room temperature for 15 h and washed with 2 N 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 2 N 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-e25e461df091492e8bfac2a75bdd5262
Source dataset
uspto-grants-2002_06
Patent number
US06410566B1

Reaction notes

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