Pyridine → HCID 20254313, compound

HRID 2418283Notes

Reaction equation

HRID 2418283 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[CH:12]3[CH2:13][CH2:14][CH2:15][CH:8]2[CH2:9][C:10](=O)[CH2:11]3)=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21].N1C=CC=CC=1>C(O)C>[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[CH:12]3[CH2:13][CH2:14][CH2:15][CH:8]2[CH2:9][C:10](=[N:20][OH:21])[CH2:11]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 20254306HCID 20254306, compound

Product 1

HCID 20254313HCID 20254313, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-methylbenzyl)-9-aza-bicyclo-[3.3.1]-nonan-3-one (5 g), hydroxylamine hydrochloride (1.5 g) and pyridine (0.75 ml) in ethanol (100 ml) was heated at reflux for 1 hour. The solution was evaporated and the residue dissolved in ethyl acetate and water. It was basified with potassium carbonate and the ethyl acetate extract was separated, dried and evaporated to give the crude oxime. Recrystallisation from ethyl acetate/light petroleum gave the oxime (4 g, 77%).

Workup

  1. temperatureat reflux for 1 hour
  2. customThe solution was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. extractionthe ethyl acetate extract
  5. customwas separated
  6. customdried
  7. customevaporated
  8. customto give the crude oxime
  9. customRecrystallisation from ethyl acetate/light petroleum

Sources & evidence

ORD record
ord-ff6989ad6c0647378ed8736c8153970f
Source dataset
uspto-grants-1984_09
Patent number
US04472413

Reaction notes

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