反应详情

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (372 mg) in tetrahydrofuran (5 mL) were added potassium tert-butoxide (123 mg) and methyl iodide (0.069 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr under a nitrogen atmosphere. To the reaction mixture were added saturated aqueous ammonium chloride solution/ethyl acetate, and the organic layer was separated, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give an oil. The obtained oil and 4-(methylamino)-1,3-thiazol-2(5H)-one (143 mg) were suspended in ethanol (5 mL), and potassium tert-butoxide (123 mg) was added. The reaction mixture was stirred at 80° C. for 3 hr. To the reaction mixture were added saturated aqueous ammonium chloride solution/ethyl acetate at room temperature, and the organic layer was separated, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (83 mg).

1. temperaturecooling
2. customthe organic layer was separated
3. washwashed with water and saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
7. customto give an oil
8. stirringThe reaction mixture was stirred at 80° C. for 3 hr
9. customthe organic layer was separated
10. washwashed with water and saturated brine
11. dry with materialdried over anhydrous magnesium sulfate
12. customthe solvent was evaporated under reduced pressure
13. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
14. customrecrystallized from ethyl acetate/heptane