反应详情

7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (2 g) was dissolved in tetrahydrofuran (25 ml), and to the solution were added thionyl chloride (0.5 ml) and N,N-dimethylformamide (catalytic amount) at room temperature under ice-cooling, and the mixture was stirred for 1.5 hours. The solvent was distilled off, the residue was dissolved in tetrahydrofuran (50 ml), and the solution was added dropwise to a solution of p-aminophenol (0.55 g) and triethylamine (2 ml) in tetrahydrofuran (25 ml) under ice-cooling. The mixture was stirred for 3 hours under nitrogen atmosphere at room temperature, and the solvent was distilled off. 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 over anhydrous magnesium sulfate, and then, the solvent was distilled off. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane), to give 7-[4-(2-butoxyethoxy)phenyl]-N-(4-hydroxyphenyl)-1-isobutyl-2,3-dihydro-1H-1-benzazepine-4-carboxamide (2 g) as pale yellow crystals.

1. temperaturecooling
2. distillationThe solvent was distilled off
3. dissolutionthe residue was dissolved in tetrahydrofuran (50 ml)
4. additionthe solution was added dropwise to a solution of p-aminophenol (0.55 g) and triethylamine (2 ml) in tetrahydrofuran (25 ml) under ice-
5. temperaturecooling
6. stirringThe mixture was stirred for 3 hours under nitrogen atmosphere at room temperature
7. distillationthe solvent was distilled off
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 over anhydrous magnesium sulfate
12. distillationthe solvent was distilled off
13. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane)