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

HRID 218331노트

반응식

HRID 218331 반응식
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

참가 물질

7

반응물 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 10942334Sodium MethoxideHCID 580978892-Benzylamino-1-(4-bromo-phenyl)-ethanol2회

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 1140Toluene용매3회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-939135b4e1194a0ca8b17b54a65b317b
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198437B2

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