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

HRID 339139Notes

Reaction equation

HRID 339139 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-09f24e05763c40c6a60807b8566963d1
Source dataset
uspto-grants-2014_11
Patent number
US08889878B2

Reaction notes

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