Benzoyl chloride → 1-benzoyl-N,N-dimethylpyrrolidine-2-carboxamide

HRID 1366667Notes

Reaction equation

HRID 1366667 reaction equation
[CH3:1][N:2]([CH3:10])[C:3](=[O:9])[C@@H:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.C(=O)(O)[O-].[Na+].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl.O>[CH3:1][N:2]([CH3:10])[C:3](=[O:9])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:23]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 7408249(2S)-N,N-dimethylpyrrolidine-2-carboxamide

Product 1

HCID 669362321-benzoyl-N,N-dimethylpyrrolidine-2-carboxamideYield 104%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

N,N-Dimethyl-L-prolinamide (2.50 g, 17.58 mmol) was dissolved in a mixture of CH2Cl2 (50 mL) and water (50 mL), then solid sodium bicarbonate (2.95 g, 35.16 mmol) was added, followed by benzoyl chloride (2.1 mL, 18.45 mmol). After stirring overnight, the phases were separated, and the aqueous phase was extracted with CH2Cl2 (3×50 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to provide N,N-dimethyl-1-(phenylcarbonyl)-L-prolinamide (4.502 g, >99%). LCMS: (M+H)+: 247.2.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with CH2Cl2 (3×50 mL)
  3. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4103c442fcbd42469e2aecacfc1c6d7c
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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