4-Chloropyridine → 4-(Diallylamino)pyridine

HRID 543290Notes

Reaction equation

HRID 543290 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:8]([NH:11][CH2:12][CH:13]=[CH2:14])[CH:9]=[CH2:10].[OH-].[Na+]>>[CH2:8]([N:11]([CH2:12][CH:13]=[CH2:14])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)[CH:9]=[CH2:10]

Participants

4

Reactant 3

HCID 122884-ChloropyridineHCID 14798Sodium HydroxideHCID 31279Diallylamine

Product 1

HCID 108776384-(Diallylamino)pyridine

Procedure

4-Chloropyridine (13.24 g) was refluxed with excess diallylamine (28.40 g) under a nitrogen atmosphere for 3 days. The product mixture was neutralized with aqueous NaOH and extracted with ether. After drying, the ether was removed by simple distillation and the product purified by fractional distillation under reduced pressure. The pure 4-(diallylamino)pyridine (DAAP) was characterized by elemental analysis, FTIR, 13C NMR, and GC.

Workup

  1. extractionextracted with ether
  2. customAfter drying
  3. customthe ether was removed by simple distillation
  4. distillationthe product purified by fractional distillation under reduced pressure

Sources & evidence

ORD record
ord-c1e96d6bd5a14c0e8569a8510d907e66
Source dataset
uspto-grants-1987_04
Patent number
US04661598

Reaction notes

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