4-(2-methyl-1-(1H)-imidazolyl)-1-phenyl-1-butanone → 4-(2-Methyl-1-(1H)-imidazolyi)-1-phenyl-1-butanone O-(2-aminoethyl)oxime dihydrochloride

HRID 1939314Notes

Reaction equation

HRID 1939314 reaction equation
[CH3:1][C:2]1[N:3]([CH2:7][CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)[CH:4]=[CH:5][N:6]=1.[ClH:18].Cl.[NH2:20][CH2:21][CH2:22][O:23][NH2:24]>C(O)C>[ClH:18].[ClH:18].[NH2:20][CH2:21][CH2:22][O:23][N:24]=[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][CH2:8][CH2:7][N:3]1[CH:4]=[CH:5][N:6]=[C:2]1[CH3:1]

Participants

4

Reactant 2

HCID 121541584-(2-methyl-1-(1H)-imidazolyl)-1-phenyl-1-butanoneHCID 143623262-(O-aminooxy)ethylamine dihydrochloride

Product 1

HCID 867510614-(2-Methyl-1-(1H)-imidazolyi)-1-phenyl-1-butanone O-(2-aminoethyl)oxime dihydrochlorideYield 109.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(2-methyl-1-(1H)-imidazolyl)-1-phenyl-1-butanone (3.00 g), O-(2-aminoethyl)hydroxylamine dihydrochloride (2.35 g), 3 equivalents of pyddine, and absolute ethanol (75 ml) was heated under reflux, under nitrogen, with stirring, for four hrs. The solvent 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 3.1 g (66%) of product, mp 153°-155° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux, under nitrogen
  3. customThe solvent was evaporated toluene
  4. additionwas added
  5. customevaporated The residue
  6. customwas 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-627ec51c553c46fa8e4e929b748494cc
Source dataset
uspto-grants-1997_12
Patent number
US05696142

Reaction notes

Loading…