Water → HCID 62735037, compound

HRID 2227487Notes

Reaction equation

HRID 2227487 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:2]=1.[H-].[Na+].[CH3:17]I.O>CN(C)C=O>[CH3:17][N:8]([CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:9](=[O:14])[C:10]([F:12])([F:13])[F:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4531450HCID 4531450, compound

Product 1

HCID 62735037HCID 62735037, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.08 g of N-(3-pyridylmethyl)trifluoroacetic acid amide was dissolved in 40 ml dimethylformamide, and then stirred with 880 mg of 60% sodium hydride on ice for 15 minutes. 1.47 ml methyl iodide was added to the reaction mixture on ice, followed by stirring at room temperature for 4 hours. After addition of water, the reaction mixture was extracted with ethyl acetate, washed with water, and then dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give a residue, which was then purified via column chromatography on silica gel (chloroform:methanol=50:1) to provide N-methyl-N-(3-pyridylmethyl)trifluoroacetic acid amide (3.71 g, 85%) as a pale yellow oil.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customto give a residue, which
  6. customwas then purified via column chromatography on silica gel (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-f75775b48a994f0ab1074990addc3971
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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