Pyridine → 3-(4-Benzyloxy-phenyl)-N-methoxy-N-methyl-propionamide

HRID 356467Notes

Reaction equation

HRID 356467 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:21][NH:22][O:23][CH3:24].N1C=CC=CC=1>S(Cl)(Cl)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]([N:22]([O:23][CH3:24])[CH3:21])=[O:19])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 5613723-(4-Benzyloxyphenyl)propionic acid

Product 1

HCID 187986593-(4-Benzyloxy-phenyl)-N-methoxy-N-methyl-propionamide

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

3-(4-Benzyloxyphenyl) propionic acid prepared in Example S (30 g, 117 mmol) was taken up in 300 mL of thionyl chloride. The reaction was kept under reflux for 5 hours, then cooled and concentrated. The residue was dissolved in 300 mL of CH2Cl2 and treated with N,O-dimethylhydroxylamine hydrochloride (14.1 g, 146 mmol) and 60 mL of pyridine at 0° C. The reaction was stirred overnight. The reaction was quenched with dilute HCl and extracted into EtOAc, and the organic layer was washed with sodium bicarbonate solution and dilute HCl and dried. The organic layer was dried (MgSO4) and concentrated. The residue was used further as crude reaction mixture or purified by flash silica gel column chromatography, eluting with EtOAc:hexane (1:9, then switching to 2:3).

Workup

  1. temperatureunder reflux for 5 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in 300 mL of CH2Cl2
  5. customThe reaction was quenched with dilute HCl
  6. extractionextracted into EtOAc
  7. washthe organic layer was washed with sodium bicarbonate solution and dilute HCl
  8. customdried
  9. dry with materialThe organic layer was dried (MgSO4)
  10. concentrationconcentrated
  11. customreaction mixture
  12. custompurified by flash silica gel column chromatography
  13. washeluting with EtOAc:hexane (1:9

Sources & evidence

ORD record
ord-2cedc33d0ff74e33835ad9a21efa296a
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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