Chloroacetyl chloride → 4-Benzyl-6-(4-bromo-phenyl)-morpholin-3-one

HRID 1896179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896179
Cl[CH2:2][C:3](Cl)=[O:4].[CH2:6]([NH:13][CH2:14][CH:15]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)[OH:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.C[O-].[Na+]>C1(C)C=CC=CC=1.CO>[CH2:6]([N:13]1[CH2:14][CH:15]([C:17]2[CH:18]=[CH:19][C:20]([Br:23])=[CH:21][CH:22]=2)[O:16][CH2:2][C:3]1=[O:4])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

7

Edukt 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 10942334Sodium MethoxideHCID 580978892-Benzylamino-1-(4-bromo-phenyl)-ethanol2×

Produkt 1

HCID 580978854-Benzyl-6-(4-bromo-phenyl)-morpholin-3-oneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel3×

Versuchsvorschrift

After addition of chloroacetyl chloride (8.49 g, 75.2 mmol) in toluene (30 ml) to a ice-cooled solution of 2-benzylamino-1-(4-bromo-phenyl)-ethanol (intermediate 31, 21.85 g, 71.4 mmol) in toluene (300 ml), a solution of triethylamine (10.25 g, 101 mmol) in toluene (20 ml) was added to the mixture and stirred for one hour. Sodium methoxide (28% solution in methanol, 45.73 g, 237 mmol) in methanol (30 ml) was then added to the solution and stirred for 2 hours. Reaction was quenched by adding dilute hydrochloric acid to adjust the pH around 7.0, and partitioned between water and ethyl acetate. The organic layer was washed with dilute hydrochloric acid, water, saturated aqueous sodium bicarbonate, and brine and dried over sodium sulfate. Solvents were removed under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=1/1) to afford 4-benzyl-6-(4-bromo-phenyl)-morpholin-3-one (intermediate 32, 21.26 g, 86%) as a colorless oil.

Aufarbeitung

  1. stirringstirred for 2 hours
  2. customReaction
  3. customwas quenched
  4. additionby adding dilute hydrochloric acid
  5. custompartitioned between water and ethyl acetate
  6. washThe organic layer was washed with dilute hydrochloric acid, water, saturated aqueous sodium bicarbonate, and brine
  7. dry with materialdried over sodium sulfate
  8. customSolvents were removed under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-94803424cf6d4ceb9d1a495ea78466bd
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518939B2

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