反应详情

In dimethylformamide (5 ml) was dissolved 7-(4-ethoxyphenyl)-1-methyl-2,3-dihydro-1-benzazepine-4-carboxylic acid hydrochloride (0.5 g), and to the mixture was added, under ice-cooling, thionyl chloride (0.25 ml). The mixture was stirred at room temperature for 45 minutes, and the solvent was evaporated. The residue was dissolved in tetrahydrofuran (15 ml), and the mixture was added dropwise to a suspension of 4-((N-(3-ethoxypropyl)-N-methylamino)methyl)aniline dihydrochloride (0.41 g) and triethylamine (1.2 ml) in tetrahydrofuran (10 ml), under ice-cooling. Under nitrogen atmosphere, the mixture was stirred at room temperature overnight, and the solvent was evaporated. To the residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (methanol/triethylamine/ethyl acetate) to give crude crystals, which were recrystallized from ethyl acetate-hexane to give N-(4-((N-(3-ethoxypropyl)-N-methylamino)methyl)phenyl)-7-(4-ethoxyphenyl)-1-methyl-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 319) (0.39 g) as pale yellow crystals.

1. additionto the mixture was added, under ice-
2. temperaturecooling
3. customthe solvent was evaporated
4. dissolutionThe residue was dissolved in tetrahydrofuran (15 ml)
5. additionthe mixture was added dropwise to a suspension of 4-((N-(3-ethoxypropyl)-N-methylamino)methyl)aniline dihydrochloride (0.41 g) and triethylamine (1.2 ml) in tetrahydrofuran (10 ml), under ice-
6. temperaturecooling
7. stirringUnder nitrogen atmosphere, the mixture was stirred at room temperature overnight
8. customthe solvent was evaporated
9. additionTo the residue was added water
10. extractionthe mixture was extracted with ethyl acetate
11. washThe organic layer was washed with water and saturated brine
12. dry with materialdried with anhydrous magnesium sulfate
13. customUnder reduced pressure, the solvent was evaporated
14. customthe residue was purified with silica gel column (methanol/triethylamine/ethyl acetate)
15. customto give crude crystals, which
16. customwere recrystallized from ethyl acetate-hexane