HCID 12906308, compound → HCID 12906310, compound

HRID 1893509Notes

Reaction equation

HRID 1893509 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[N:10](C)[C:11](=O)OC(C)(C)C.[ClH:19].O1CCOCC1>ClCCl.C(O)C.O>[ClH:19].[CH3:11][NH:10][N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1

Participants

6

Reactant 2

HCID 12906308HCID 12906308, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 12906310HCID 12906310, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

The compound (126 g) obtained in step B was dissolved in a mixed solvent of dichloromethane (150 ml) and ethanol (150 ml). A 4N hydrochloric acid-dioxane solution (500 ml) was added with stirring at room temperature and the mixture was stirred at the same temperature for 5 hr. The reaction mixture was diluted with dichloromethane and water and the aqueous layer was extracted. An ice-cooled aqueous sodium hydroxide solution was added to the ice-cooled aqueous layer to give a strongly-alkaline aqueous layer. The aqueous layer was extracted with dichloromethane. The organic layer was dried over potassium carbonate, and the insoluble material was filtered off. The solvent was evaporated under reduced pressure. The obtained oil was dissolved in diethyl ether (500 ml), and 4N hydrochloric acid-dioxane solution (140 ml) was added with stirring under ice-cooling to allow precipitation of a solid. This was filtered, washed with diethyl ether, and dried under reduced pressure to give the title compound (75.89 g, yield 81%) as a gray solid.

Workup

  1. stirringthe mixture was stirred at the same temperature for 5 hr
  2. extractionthe aqueous layer was extracted
  3. temperatureAn ice-cooled aqueous sodium hydroxide solution
  4. additionwas added to the ice-
  5. temperaturecooled aqueous layer
  6. customto give a strongly-alkaline aqueous layer
  7. extractionThe aqueous layer was extracted with dichloromethane
  8. dry with materialThe organic layer was dried over potassium carbonate
  9. filtrationthe insoluble material was filtered off
  10. customThe solvent was evaporated under reduced pressure
  11. dissolutionThe obtained oil was dissolved in diethyl ether (500 ml)
  12. addition4N hydrochloric acid-dioxane solution (140 ml) was added
  13. stirringwith stirring under ice-
  14. temperaturecooling
  15. customprecipitation of a solid
  16. filtrationThis was filtered
  17. washwashed with diethyl ether
  18. customdried under reduced pressure

Sources & evidence

ORD record
ord-2fde618d2b104539a06795ce9f2cbda7
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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