Benzylamine → N-benzyl-3,5,6-trifluoropyridin-2-amine

HRID 368398Notes

Reaction equation

HRID 368398 reaction equation
F[C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[N:3]=1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(#N)C>[CH2:11]([NH:18][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]([F:10])[N:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 1377492,3,5,6-Tetrafluoropyridine

Product 1

HCID 22121263N-benzyl-3,5,6-trifluoropyridin-2-amineYield 84.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 50 ml of acetonitrile were added 12.0 g of 2,3,5,6-tetrafluoropyridine and 18.0 g of benzylamine, and the mixture was stirred under reflux condition for 2 hours, and the solvent and the like were distilled off. To the residue was added 150 ml of ethyl acetate, and the mixture was washed twice with 150 ml of distilled water and 150 ml of 10% aqueous solution of citric acid. The ethyl acetate layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 16.0 g of the title compound as a pale yellow oil.

Workup

  1. temperatureunder reflux condition for 2 hours
  2. distillationthe solvent and the like were distilled off
  3. additionTo the residue was added 150 ml of ethyl acetate
  4. washthe mixture was washed twice with 150 ml of distilled water and 150 ml of 10% aqueous solution of citric acid
  5. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-640ab0b2c6114dd48a9f9bf176ea369f
Source dataset
uspto-grants-2000_10
Patent number
US06133284

Reaction notes

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