1,4-Dioxane hydrochloride → HCID 58452462, compound

HRID 70588Notes

Reaction equation

HRID 70588 reaction equation
O1CCOCC1.Cl.[CH:8]1(/[CH:13]=[C:14](/[C:23]2[N:28]=[C:27]([O:29]C)[C:26]([CH:31]3[CH2:33][CH2:32]3)=[CH:25][CH:24]=2)\[C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1>O>[CH:8]1(/[CH:13]=[C:14](/[C:23]2[NH:28][C:27](=[O:29])[C:26]([CH:31]3[CH2:33][CH2:32]3)=[CH:25][CH:24]=2)\[C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)[CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67398814HCID 67398814, compound

Product 1

HCID 58452462HCID 58452462, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A 4 M hydrogen chloride-1,4-dioxane solution (4.5 mL) was added to a suspension of 6-{(E)-2-cyclopentyl-1-[4-(methylsulfanyl)phenyl]ethenyl}-3-cyclopropyl-2-methoxypyridine (150 mg) in water (1.5 mL), and the mixture was stirred at 90° C. for 1.5 hours. The reaction solution was cooled to room temperature and extracted with chloroform twice. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in a hexane-ethyl acetate solution with heating, and then recrystallization by cooling to room temperature gave the title compound as a colorless powder (111 mg, 77%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextracted with chloroform twice
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationafter which the filtrate was concentrated under reduced pressure
  7. dissolutionThe resulting residue was dissolved in a hexane-ethyl acetate solution
  8. temperaturewith heating
  9. customrecrystallization
  10. temperatureby cooling to room temperature

Sources & evidence

ORD record
ord-79c625bb3d3e4e498c678f826ee938a1
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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