Pyridine → 2-[4-Fluoro-3-(trifluoromethyl)phenoxy]-N-(phenylmethyl)butanamide

HRID 1651472Notes

Reaction equation

HRID 1651472 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[F:15][C:16]1[CH:28]=[CH:27][C:19]([O:20][CH:21]([CH2:25][CH3:26])[C:22](Cl)=[O:23])=[CH:18][C:17]=1[C:29]([F:32])([F:31])[F:30]>C1(C)C=CC=CC=1>[CH2:1]([NH:8][C:22](=[O:23])[CH:21]([O:20][C:19]1[CH:27]=[CH:28][C:16]([F:15])=[C:17]([C:29]([F:31])([F:32])[F:30])[CH:18]=1)[CH2:25][CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7504BenzylamineHCID 14391759HCID 14391759, compound

Product 1

HCID 64511592-[4-Fluoro-3-(trifluoromethyl)phenoxy]-N-(phenylmethyl)butanamideYield 92.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In accordance with the above reaction formula (1), the compound of the present invention was prepared. First, after 4.2 g (0.039 mole) of benzylamine and 3.1 g (0.039 mole) of pyridine were dissolved in 50 ml of toluene, 11.0 g (0.039 mole) of 2-(4-fluoro-3-trifluoromethylphenoxy)butanoic chloride was gradually added dropwise to the solution under stirring at room temperature. After dropwise addition, the mixture was further stirred for 3 hours at room temperature, and the reaction mixture was then washed with a diluted hydrochloric acid, diluted sodium hydroxide and water with the order. After the toluene layer was dehydrated with anhydrous sodium sulfate, toluene was distilled out under reduced pressure. Resulting crude crystal was recrystallized from toluene to give 12.8 g (Yield: 92 %) of N-benzyl-2-(4-fluoro-3-trifluoromethylphenoxy)butanoic amide having a melting point of 75 to 76 ° C. as colorless needle crystals. Elemental analysis

Workup

  1. additionAfter dropwise addition
  2. stirringthe mixture was further stirred for 3 hours at room temperature
  3. washthe reaction mixture was then washed with a diluted hydrochloric acid, diluted sodium hydroxide and water with the order
  4. distillationwas distilled out under reduced pressure
  5. customResulting crude crystal
  6. customwas recrystallized from toluene

Sources & evidence

ORD record
ord-32b67908f3c44cbb810d54b827aa2a2b
Source dataset
uspto-grants-1990_05
Patent number
US04929273

Reaction notes

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