Triethylamine → HCID 19756146, compound

HRID 1587706Notes

Reaction equation

HRID 1587706 reaction equation
[CH2:1]([C:12]1[CH:17]=[CH:16][N+:15]([O-])=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH2:19]([N:21](CC)CC)C>C(#N)C>[C:19]([C:16]1[CH:17]=[C:12]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:13]=[CH:14][N:15]=1)#[N:21]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 2751821HCID 2751821, compound

Product 1

HCID 19756146HCID 19756146, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5.00 g (20 mmol) of 4-n-undecylpyridine N-oxide and 4.04 g (40 mmol) of triethylamine dissolved in 20 ml of acetonitrile was dropwise added 7.92 g of trimethylsilylanilide while stirring at room temperature. After the dropwise addition, the mixture was refluxed for 22 hours, concentrated under a reduced pressure, then dissolved in diethyl ether and washed with saturated sodium hydrogen carbonate solution. The product was dried over anhydrous aqueous sodium sulfate and concentrated under a reduced pressure, followed by separation by silica gel column chromatography (ethyl acetate:hexane=1:9) to give the desired product of 3.95 g (solidified) (yield 76.2%).

Workup

  1. additionAfter the dropwise addition
  2. temperaturethe mixture was refluxed for 22 hours
  3. concentrationconcentrated under a reduced pressure
  4. dissolutiondissolved in diethyl ether
  5. washwashed with saturated sodium hydrogen carbonate solution
  6. dry with materialThe product was dried over anhydrous aqueous sodium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customfollowed by separation by silica gel column chromatography (ethyl acetate:hexane=1:9)

Sources & evidence

ORD record
ord-57213499d3d44329a28a87e31d6a8fe4
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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