Acetic Acid → HCID 178526255, compound

HRID 131107Notes

Reaction equation

HRID 131107 reaction equation
N1([CH:7]2[CH2:12][O:11][N:10]=[C:9]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)[N:8]2C)CCCCC1.[C:20](O)(=O)[CH3:21].OS(O)(=O)=O.OO.[OH2:31]>>[N:8]1([CH2:7][CH:7]2[CH2:12][O:11][N:10]=[C:9]([C:13]3[CH:14]=[N+:15]([O-:31])[CH:16]=[CH:17][CH:18]=3)[NH:8]2)[CH2:21][CH2:20][CH2:18][CH2:13][CH2:9]1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 784Hydrogen Peroxide2×HCID 962WaterHCID 1118Sulfuric AcidHCID 68692493HCID 68692493, compound

Product 1

HCID 178526255HCID 178526255, compound

Conditions

Temperature
60 °C

Procedure

6.25 g (24 mmol) of (−)-5,6-dihydro-5-(1-piperidinyl)-methyl-3-(3-pyridyl)4H-1,2,4-oxadiazine is dissolved in a mixture of 40 ml of water, 6.85 ml (120 mmol) of glacial acetic acid and 1.43 ml (24 mmol) of cc. H2SO4. The solution is heated to 60° C., and at this temperature 12 ml (75 mmol) of 21.5% hydrogen peroxide is added dropwise, and the reaction mixture is kept on stirring at this temperature. After 10 hours to the reaction mixture further 6 ml of 21.5% hydrogen peroxide is added dropwise. After another 20 hours the reaction mixture is cooled to 0° C., and it is introduced dropwise into 60 ml of 0° C. 20% NaOH, then extracted 5 times with 50 ml of dichloromethane. The combined organic phases are washed with water, dried over magnesium-sulfate and evaporated. The evaporation residue is purified by column chromatography. The suitable fractions are triturated with 20 ml of acetone and kept in refrigerator overnight. Next day the product is filtered, washed with cold acetone and dried, then recrystallized from ethanol-ethylacetate.

Workup

  1. temperatureAfter another 20 hours the reaction mixture is cooled to 0° C.
  2. additionit is introduced dropwise into 60 ml of 0° C
  3. extraction20% NaOH, then extracted 5 times with 50 ml of dichloromethane
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over magnesium-sulfate
  6. customevaporated
  7. customThe evaporation residue is purified by column chromatography
  8. customThe suitable fractions are triturated with 20 ml of acetone
  9. customkept in refrigerator overnight
  10. filtrationNext day the product is filtered
  11. washwashed with cold acetone
  12. customdried
  13. customrecrystallized from ethanol-ethylacetate

Sources & evidence

ORD record
ord-7b8123a7563f4c62af8c4c3bae119d84
Source dataset
uspto-grants-2008_06
Patent number
US07384936B2

Reaction notes

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