反应详情

A solution of N-[5-(bromoacetyl)-2-(phenylmethoxy)phenyl]methanesulphonamide (1.96 g), N-[6-[4-[(2-naphthalenyl)oxy]butoxy]hexyl]benzenemethanamine (2.0 g) and DEA (0.96 g) in dichloromethane (45 ml) was stirred under nitrogen at room temperature for 22 h. The mixture was treated with water (100 ml) and extracted with dichloromethane (2×150 ml). The combined organic extracts were dried and evaporated in vacuo to give an oil which was dissolved in methanol (30 ml) and dichloromethane (20 ml) and cooled to 0°-5° C. under nitrogen. Sodium borohydride (0.50 g) was added portionwise and the solution stirred at room temperature for 30 min, then carefully diluted with water (20 ml). The solvent was evaporated in vacuo, the residue partitioned between water (100 ml) and dichloromethane (150 ml) and the aqueous phase re-extracted with dichloromethane (150 ml), the combined organic extracts being dried and evaporated in vacuo to give an oil which was purified by FCC eluting with System C (95:5:1). A solution of the oil (3.41 g) in absolute ethanol (60 ml) was hydrogenated over pre-reduced 10% palladium on charcoal catalyst (50% aqueous paste, 1.5 g) in absolute ethanol (10 ml) for 4.5 h. The mixture was filtered through hyflo and evaporated in vacuo to give an oil which was purified by FCC eluting with System B (40:10:1) to give a cream solid. Trituration with diethyl ether gave the title compound as a white solid (1.23 g), m.p. 99.5°-100.5°.

1. extractionextracted with dichloromethane (2×150 ml)
2. customThe combined organic extracts were dried
3. customevaporated in vacuo
4. customto give an oil which
5. customThe solvent was evaporated in vacuo
6. customthe residue partitioned between water (100 ml) and dichloromethane (150 ml)
7. extractionthe aqueous phase re-extracted with dichloromethane (150 ml)
8. customthe combined organic extracts being dried
9. customevaporated in vacuo
10. customto give an oil which
11. customwas purified by FCC
12. washeluting with System C (95:5:1)
13. waitA solution of the oil (3.41 g) in absolute ethanol (60 ml) was hydrogenated over pre-reduced 10% palladium on charcoal catalyst (50% aqueous paste, 1.5 g) in absolute ethanol (10 ml) for 4.5 h
14. filtrationThe mixture was filtered through hyflo
15. customevaporated in vacuo
16. customto give an oil which
17. customwas purified by FCC
18. washeluting with System B (40:10:1)
19. customto give a cream solid