Chloroacetyl chloride → 4-Benzyl-5-(hydroxymethyl)-5-methylmorpholin-3-one

HRID 584228

Reaktionsgleichung

Reaktionsgleichung von HRID 584228
Cl[CH2:2][C:3](Cl)=[O:4].[CH2:6]([NH:13][C:14]([CH3:19])([CH2:17][OH:18])[CH2:15][OH:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[CH2:6]([N:13]1[C:14]([CH2:17][OH:18])([CH3:19])[CH2:15][O:16][CH2:2][C:3]1=[O:4])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 1987392-(Benzylamino)-2-methylpropane-1,3-diol

Produkt 1

HCID 223427394-Benzyl-5-(hydroxymethyl)-5-methylmorpholin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Chloroacetyl chloride (14.0 ml) was added dropwise to a mixture of 2-benzylamino-2-methyl-1,3-propanediol (28.5 g), potassium carbonate (30.3 g) in dichloromethane (150 ml) and water (150 ml) at 0° C., and the whole was stirred at room temperature for 2 hours. The mixture was extracted with dichloromethane and the extract was washed successively with water, 1N hydrochloric acid and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was dissolved in tert-butanol (400 ml) and the solution was added potassium tert-butoxide (16.38 g) portionwisely and the whole was refluxed for 30 minutes. After cooling, the solvent was removed by evaporation and ethyl acetate and water were added thereto. The organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane (1:1) as an eluent to give 4-benzyl-5-hydroxymethyl-5-methyl-3-morpholinone (10.89 g).

Aufarbeitung

  1. extractionThe mixture was extracted with dichloromethane
  2. washthe extract was washed successively with water, 1N hydrochloric acid and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved in tert-butanol (400 ml)
  6. additionthe solution was added potassium tert-butoxide (16.38 g) portionwisely
  7. temperaturethe whole was refluxed for 30 minutes
  8. temperatureAfter cooling
  9. customthe solvent was removed by evaporation and ethyl acetate and water
  10. additionwere added
  11. customThe organic layer was separated
  12. dry with materialdried over magnesium sulfate
  13. customevaporated in vacuo
  14. customThe residue was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane (1:1) as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-75473a4fa51645e18d3a4f6e822d4c71
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924278B2

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