Pyridine → HCID 86751063, compound

HRID 1939318Notes

Reaction equation

HRID 1939318 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[CH3:17])=[CH:4][CH:3]=1.[ClH:19].Cl.[NH2:21][CH2:22][CH2:23][O:24][NH2:25].N1C=CC=CC=1>C(O)C>[ClH:19].[ClH:19].[NH2:21][CH2:22][CH2:23][O:24][N:25]=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:9][CH2:10][CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12154159HCID 12154159, compoundHCID 143623262-(O-aminooxy)ethylamine dihydrochloride

Product 1

HCID 86751063HCID 86751063, compoundYield 116%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-4-(2-methyl-1-(1H)-imidazolyl)-1-butanone (3.00 g), O-(2-aminoethyl)hydroxylamine dihydrochloride (2.18 g), 3 equivalents of pyridine, and absolute ethanol (75 ml) was heated under reflux, under nitrogen, with stirring, for three hrs. The reaction mixture was evaporated, toluene was added and evaporated. The residue was partitioned between 10% sodium hydroxide solution and ethyl acetate. The layers were separated and the aqueous phase extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated. The residue was purified by flash chromatography (180:19:1 dichloromethane/methanol/ammonium hydroxide). The appropriate fractions were collected and concentrated. The residue was dissolved in absolute ethanol and treated with ethereal hydrogen chloride. Diethyl ether was added. The precipitate was collected and recrystallized from absolute ethanol/ether to give 3.2 g (70%) of product, mp 219°-221° C. (dec).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux, under nitrogen
  3. customThe reaction mixture was evaporated
  4. additiontoluene was added
  5. customevaporated
  6. customThe residue was partitioned between 10% sodium hydroxide solution and ethyl acetate
  7. customThe layers were separated
  8. extractionthe aqueous phase extracted with ethyl acetate
  9. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customthe filtrate was evaporated
  12. customThe residue was purified by flash chromatography (180:19:1 dichloromethane/methanol/ammonium hydroxide)
  13. customThe appropriate fractions were collected
  14. concentrationconcentrated
  15. dissolutionThe residue was dissolved in absolute ethanol
  16. additiontreated with ethereal hydrogen chloride
  17. additionDiethyl ether was added
  18. customThe precipitate was collected
  19. customrecrystallized from absolute ethanol/ether

Sources & evidence

ORD record
ord-b7580987d3d240efbc6587046006ce49
Source dataset
uspto-grants-1997_12
Patent number
US05696142

Reaction notes

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