Pyridine → N-methoxy-N-methyl-3-phenylpropanamide

HRID 230880

Reaction equation

HRID 230880 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].N1C=CC=CC=1.[C:12]1([CH2:18][CH2:19][C:20](Cl)=[O:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[CH3:5][O:4][N:3]([CH3:2])[C:20](=[O:21])[CH2:19][CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 64801Benzenepropanoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 3785569N-methoxy-N-methyl-3-phenylpropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N,O-dimethylhydroxylamine hydrochloride (1.1 g) and pyridine (1.82 mL) in dichloromethane (50 mL) was added 3-phenylpropionyl chloride (1.52 mL) under ice-cooling, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added 1 mol/L hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (1.89 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue was added 1 mol/L hydrochloric acid
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fc82fba548ad4b1f9d02f8cff2363540
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Linked notes

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