反应详情

To a solution of 3-(3-cyanophenyl)-1-phenyl-2-propen-1-one (4.7 g) in methyl isobutyl ketone (50 ml) were added N-(2-morpholinoethyl)acetoacetamide (6.5 g) and ammonium acetate (2.3 g), and the mixture was stirred at 80° to 85° C. for 4 hours. After cooling, the reaction mixture was washed with water and dried over magnesium sulfate. To the filtrate containing 1,4-dihydro-3-(2-morpholinoethylcarbamoyl)-2-methyl-4-(3-cyanophenyl)-6-phenylpyridine and 3-(2-morpholinoethylcarbamoyl)-2-methyl-4-(3-cyanophenyl)-6-phenylpyridine was added manganese dioxide (20 g) and the resultant mixture was stirred at 80° to 85° C. for 1.5 hours. Manganese dioxide was filtered off, and the filtrate was concentrated in vacuo. The residue was dissolved in diluted hydrochloric acid and washed with ethyl acetate. The aqueous layer was adjusted to pH 8.0 with 20% aqueous solution of potassium carbonate, and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was subjected to a column chromatography on silica gel and eluted with a mixture of ethyl acetate and tetrahydrofuran (8:2 V/V). The fractions containing the desired compound were combined and concentrated in vacuo. The residue was recrystallized from diethyl ether to give 3-(2-morpholinoethylcarbamoyl)-2-methyl-4-(3-cyanophenyl)-6-phenylpyridine (2.55 g).

1. temperatureAfter cooling
2. washthe reaction mixture was washed with water
3. dry with materialdried over magnesium sulfate
4. additionTo the filtrate containing 1,4-dihydro-3-(2-morpholinoethylcarbamoyl)-2-methyl-4-(3-cyanophenyl)-6-phenylpyridine and 3-(2-morpholinoethylcarbamoyl)-2-methyl-4-(3-cyanophenyl)-6-phenylpyridine
5. additionwas added manganese dioxide (20 g)
6. stirringthe resultant mixture was stirred at 80° to 85° C. for 1.5 hours
7. filtrationManganese dioxide was filtered off
8. concentrationthe filtrate was concentrated in vacuo
9. dissolutionThe residue was dissolved in diluted hydrochloric acid
10. washwashed with ethyl acetate
11. extractionextracted with ethyl acetate
12. washThe extract was washed with brine
13. dry with materialdried over magnesium sulfate
14. customThe solvent was evaporated in vacuo
15. washeluted with a mixture of ethyl acetate and tetrahydrofuran (8:2 V/V)
16. additionThe fractions containing the desired compound
17. concentrationconcentrated in vacuo
18. customThe residue was recrystallized from diethyl ether