反应详情

In THF (5 ml) was dissolved 1-benzyl-7-[4-(2-butoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.3 g). Under ice-cooling, to the solution were added oxalyl (0.11 ml) and DMF (catalytic amount). The mixture was stirred at room temperature for 30 minutes, and the solvent was evaporated under reduced pressure. In THF (25 ml) was dissolved the residue, the solution was added dropwise to a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.15 g) and triethylamine (0.44 ml) in THF (10 ml), under ice-cooling. The mixture was stirred at room temperature under nitrogen atmosphere and the solvent was evaporated under reduced pressure. 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. The solvent was evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol/triethylamine) to give crude crystals, which were recrystallized from ethyl acetate-hexane to give 1-benzyl-7-[4-(2-butoxyethoxy)phenyl]-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 33) (0.26 g) as pale yellow crystals.

1. temperatureUnder ice-cooling, to the solution
2. customthe solvent was evaporated under reduced pressure
3. dissolutionIn THF (25 ml) was dissolved the residue
4. additionthe solution was added dropwise to a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.15 g) and triethylamine (0.44 ml) in THF (10 ml), under ice-
5. temperaturecooling
6. stirringThe mixture was stirred at room temperature under nitrogen atmosphere
7. customthe solvent was evaporated under reduced pressure
8. additionTo the residue was added water
9. extractionthe mixture was extracted with ethyl acetate
10. washThe organic layer was washed with water and saturated brine
11. dry with materialdried with anhydrous magnesium sulfate
12. customThe solvent was evaporated
13. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol/triethylamine)
14. customto give crude crystals, which
15. customwere recrystallized from ethyl acetate-hexane