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

HRID 339139ノート

反応式

HRID 339139 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-09f24e05763c40c6a60807b8566963d1
出典データセット
uspto-grants-2014_11
特許番号
US08889878B2

反応ノート

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