Triethylamine → HCID 19780236, compound

HRID 2081578Notes

Reaction equation

HRID 2081578 reaction equation
C[Si]([C:5]#[N:6])(C)C.[CH2:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N+:15]=1[O-])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(#N)C>[CH2:7]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:5]#[N:6])[N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 3155902-Benzyl-1-oxo-1lambda~5~-pyridine

Product 1

HCID 19780236HCID 19780236, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trimethylsilyl cyanide (14.56 g, 19.6 ml, 0.147 moles) was added dropwise to a solution of 2-benzylpyridine-N-oxide (10.86 g, 0.059 moles) and triethylamine (8.91 g, 12.3 ml, 0.088 moles) in acetonitrile (40 ml) at 20° C. After complete addition the mixture was heated under reflux for 20 hours, cooled to room temperature and partitioned between methylene chloride and saturated sodium bicarbonate. The organic layer was washed with water and saturated sodium chloride, and then dried over anhydrous magnesium sulphate. Removal of the solvent gave an orange oil which was purified by column chromatography (silica gel eluted with hexane:ethyl acetate 9:1) to give 2-benzyl-6-cyanopyridine (1.84 g, 16%) as a pale yellow oil.

Workup

  1. additionAfter complete addition the mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 20 hours
  4. custompartitioned between methylene chloride and saturated sodium bicarbonate
  5. washThe organic layer was washed with water and saturated sodium chloride
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customRemoval of the solvent
  8. customgave an orange oil which
  9. customwas purified by column chromatography (silica gel eluted with hexane:ethyl acetate 9:1)

Sources & evidence

ORD record
ord-5379ca734dae47c68f9e767c9df4b3cd
Source dataset
uspto-grants-1993_02
Patent number
US05185339

Reaction notes

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