Potassium Carbonate → 2-[2-(3-bromo-phenyl)-2-hydroxy-ethylamino]-N-phenyl-acetamide

HRID 560116

반응식

HRID 560116 반응식
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)[OH:4].Cl[CH2:13][C:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15].C(=O)([O-])[O-].[K+].[K+].OP([O-])(O)=O.[K+]>C(#N)C.C(OCC)(=O)C>[Br:11][C:7]1[CH:6]=[C:5]([CH:3]([OH:4])[CH2:2][NH:1][CH2:13][C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:15])[CH:10]=[CH:9][CH:8]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 11485ChloroacetanilideHCID 516951Monobasic potassium phosphateHCID 220210672-Amino-1-(3-bromophenyl)ethan-1-ol

생성물 1

HCID 670006572-[2-(3-bromo-phenyl)-2-hydroxy-ethylamino]-N-phenyl-acetamide수율 42.3%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a solution of 2-amino-1-(3-bromo-phenyl)-ethanol (example 33, step 1, 1.34 g) and crude 2-chloro-N-phenyl-acetamide (example 33, step 2, 1.0 g) in acetonitrile (15 mL) was added potassium carbonate (1.03 g). The mixture was heated to 80° C. overnight. A 1M solution of KH2PO4 was added, followed by ethyl acetate. The phases were separated, and the inorganic one was extracted with ethyl acetate (x2). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo. Column chromatography (SiO2, CH2Cl2/MeOH 95:5) followed by precipitation from a mixture of diethylether/n-heptane (1:4) gave 2-[2-(3-bromo-phenyl)-2-hydroxy-ethylamino]-N-phenyl-acetamide (0.87 g, 42%) as a white solid, MS: 349.1 (M+H, 1Br)+.

후처리

  1. customThe phases were separated
  2. extractionthe inorganic one was extracted with ethyl acetate (x2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customColumn chromatography (SiO2, CH2Cl2/MeOH 95:5) followed by precipitation from a mixture of diethylether/n-heptane (1:4)

출처 및 근거

ORD 기록
ord-e54f51f2b32547079b951d7506d0e604
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063088B2

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