Propionyl chloride → N-[1-(4-bromo-2-fluorophenyl)ethyl]propanamide

HRID 339139노트

반응식

HRID 339139 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:10])[CH3:9])=[C:4]([F:11])[CH:3]=1.[C:12](Cl)(=[O:15])[CH2:13][CH3:14].CCN(C(C)C)C(C)C>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][C:12](=[O:15])[CH2:13][CH3:14])[CH3:9])=[C:4]([F:11])[CH:3]=1

참가 물질

5

반응물 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 185435761-(4-Bromo-2-fluorophenyl)ethan-1-amine

생성물 1

HCID 58247950N-[1-(4-bromo-2-fluorophenyl)ethyl]propanamide수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

61 mg (1 eq, 0.24 mmol) of 1-(4-bromo-2-fluorophenyl)ethanamine from Stage 1 were dissolved in 4 ml of dichloromethane, and 24 mg (1.1 eq, 23 μl, 0.264 mmol) of propanoyl chloride and 70 mg (2.2 eq, 90 μl) of Hünig's base were added. The mixture was stirred at room temperature for 5 h and then concentrated. The crude product was dissolved in ethyl acetate and washed 1× with 1M HCl, 1× with sat. sodium carbonate solution and then with water, and dried over magnesium sulphate. After concentrating under reduced pressure, the resulting crude product was purified by means of chromatography on silica gel (eluent: cyclohexane/ethyl acetate). 50 mg (67%) of N-[1-(4-bromo-2-fluorophenyl)ethyl]propanamide were obtained.

후처리

  1. concentrationconcentrated
  2. dissolutionThe crude product was dissolved in ethyl acetate
  3. washwashed 1× with 1M HCl, 1× with sat. sodium carbonate solution
  4. dry with materialwith water, and dried over magnesium sulphate
  5. concentrationAfter concentrating under reduced pressure
  6. customthe resulting crude product was purified by means of chromatography on silica gel (eluent: cyclohexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-09f24e05763c40c6a60807b8566963d1
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889878B2

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