Potassium Cyanide → 4-(Pyridin-4-YL)butanenitrile

HRID 1756546Notes

Reaction equation

HRID 1756546 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.[C-:11]#[N:12].[K+]>C(#N)C.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>[N:8]1[CH:9]=[CH:10][C:5]([CH2:4][CH2:3][CH2:2][C:11]#[N:12])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 2054424-(3-Chloropropyl)pyridine

Product 1

HCID 135575314-(Pyridin-4-YL)butanenitrileYield 84.5%

Reagents, catalysts & solvents 2

HCID 26541Dibenzo-18-crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

To the product of Example 21(6.7 g, 42.9 mmol) in 300 mL of acetonitrile (CH3CN), was added potassium cyanide (KCN, 11.2 g, 171.7 mmol) and dibenzo-18-crown-6 (1.0 g, 2.8 mmol). After the reaction had been refluxed for 18 hours, it was cooled to room temperature, and stripped of all solvent under reduced pressure. The residue was partitioned between 100 mL each of water and CH2Cl2 and the aqueous phase was washed with 3×100 mL of CH2Cl2. The combined organic phase was dried (Na2SO4), filtered, and stripped of solvent to yield 6.7 g of crude product. This material was purified by HPLC on silica gel to yield 5.3 g of the title material as a yellow oil.

Workup

  1. temperatureAfter the reaction had been refluxed for 18 hours
  2. customThe residue was partitioned between 100 mL each of water and CH2Cl2
  3. washthe aqueous phase was washed with 3×100 mL of CH2Cl2
  4. dry with materialThe combined organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customto yield 6.7 g of crude product
  7. customThis material was purified by HPLC on silica gel

Sources & evidence

ORD record
ord-cf3882ed8da24a34a5e54a1eebf824f5
Source dataset
uspto-grants-1995_08
Patent number
US05441950

Reaction notes

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