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

HRID 2417819Notes

Reaction equation

HRID 2417819 reaction equation
[C-]#N.[K+].C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1.Cl[CH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1.OCCCC1C=C[N:47]=[CH:46]C=1>C(#N)C>[C:46]([CH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1)#[N:47]

Participants

6

Reactant 4

HCID 9032Potassium CyanideHCID 26541Dibenzo-18-crown-6HCID 729234-PyridinepropanolHCID 2054424-(3-Chloropropyl)pyridine

Product 1

HCID 135575314-(Pyridin-4-YL)butanenitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium cyanide (11.18 g) and dibenzo-18-crown-6 (1.0 g) are added to a solution of 4-(3-chloropropyl)pyridine (6.68 g) prepared from 4-(3-hydroxypropyl)pyridine, in 300 ml of dry acetonitrile under nitrogen. The mixture is refluxed for 24 hours, the solvent evaporated and the residue partitioned between methylene chloride and water. The aqueous phase is further extracted with methylene chloride (3×100 ml) and the combined extracts are dried over sodium sulfate, decolorized with charcoal and evaporated to yield 4-(3-cyanopropyl)pyridine as a colorless oil.

Workup

  1. temperatureThe mixture is refluxed for 24 hours
  2. customthe solvent evaporated
  3. customthe residue partitioned between methylene chloride and water
  4. extractionThe aqueous phase is further extracted with methylene chloride (3×100 ml)
  5. dry with materialthe combined extracts are dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-c704c905eb4742d091abdd0ddc6fbce7
Source dataset
uspto-grants-1984_09
Patent number
US04470986

Reaction notes

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