Triethylamine → HCID 11052524, compound

HRID 1861779Notes

Reaction equation

HRID 1861779 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][N+:11]([O-])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[CH2:16][N:17](CC)CC.C[Si](C#N)(C)C>C(#N)C.C(Cl)Cl>[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:16]#[N:17])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 3155894-Benzyl-1-oxo-1lambda~5~-pyridine

Product 1

HCID 11052524HCID 11052524, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-benzylpyridine-N-oxide (8.8 g, 48 mmol) in acetonitrile (50 mL) was added Et3N (9.9 mL, 71.2 mmol). Neat trimethylsilyl cyanide (15.8 mL, 118 mmol) was added dropwise. The resulting solution was heated at reflux for 10 h under nitrogen then after cooling, diluted with CH2Cl2 (150 mL). The resulting solution was washed with NaHCO3 (2×150 mL), dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by filtration on silica gel using EtOAc/n-hexane as eluant to afford the title compound as a pale yellow oil (7.2 g, 78%): 1H NMR (CDCl3) δ4.03 (s, 2H), 7.16 (d, J=7.2 Hz, 2H), 7.20-7.40 (m, 4H), 7.49 (s, 1H), 8.59 (d, J=5.1 Hz, 1H); IR (film) 2240, 1600, 1500 cm−1.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 10 h under nitrogen
  3. temperatureafter cooling
  4. washThe resulting solution was washed with NaHCO3 (2×150 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. filtrationThe crude compound was purified by filtration on silica gel

Sources & evidence

ORD record
ord-28b55d320e9b40808279251badb3795b
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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