反应详情

In DMF (6 ml) was dissolved 1-phenyl-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.2 g). Under ice-cooling, to the mixture was added thionyl chloride (0.08 ml). The mixture was stirred at room temperature for 30 minutes. The solvent was evaporated under reduced pressure. In THF (20 ml) was suspended the residue, the suspension was added dropwise to a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.12 g) and triethylamine (0.31 ml) in THF (5 ml), under ice-cooling. The mixture was stirred at room temperature overnight under nitrogen atmosphere. The solvent was evaporated under reduced pressure. Water was added to the mixture, 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, the residue was purified with silica gel column chromatography (ethyl acetate/methanol/triethylamine), which was dissolved in ethyl acetate-ethanol, 4N hydrochloric acid-ethyl acetate was added to the solution, and the solvent was evaporated to give 1-phenyl-7-[4-(2-propoxyethoxy)phenyl]-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide hydrochloride (Compound 38) (0.17 g) as yellow crystals.

1. temperatureUnder ice-cooling, to the mixture
2. customThe solvent was evaporated under reduced pressure
3. additionthe suspension was added dropwise to a solution of 4-[N-methyl-N-(tetrahydro-2H-pyran-4-yl)aminomethyl]aniline (0.12 g) and triethylamine (0.31 ml) in THF (5 ml), under ice-
4. temperaturecooling
5. stirringThe mixture was stirred at room temperature overnight under nitrogen atmosphere
6. customThe solvent was evaporated under reduced pressure
7. additionWater was added to the mixture
8. extractionthe mixture was extracted with ethyl acetate
9. washThe organic layer was washed with water and saturated brine
10. dry with materialdried with anhydrous magnesium sulfate
11. customThe solvent was evaporated
12. customthe residue was purified with silica gel column chromatography (ethyl acetate/methanol/triethylamine), which
13. dissolutionwas dissolved in ethyl acetate-ethanol
14. addition4N hydrochloric acid-ethyl acetate was added to the solution
15. customthe solvent was evaporated