反应详情

1.6 g (9.5 mmol) of N-[8-azabicyclo[3.2.1]oct-3-yl]acetamide prepared according to Dostert et al. (European Journal of Medicinal Chemistry 1984, 19 (2), 105-110) are dissolved in 45 mL of acetone, and 5.2 g of potassium carbonate and 2.5 g (11.4 mmol) of 2-(bromomethyl)naphthalene are added. The mixture is refluxed with stirring for 18 hours. After cooling, the acetone is partially evaporated off. Water is added to the residue, and the mixture is extracted with dichloromethane. The organic phase is extracted with 1N hydrochloric acid. The acidic aqueous phase obtained is basified with 1N sodium hydroxide and then extracted with dichloromethane. The extract is washed with water and with brine, dried over anhydrous sodium sulfate and then evaporated under reduced pressure. The residue obtained is filtered on silica gel (solvent: 95/5 (v/v) dichloromethane/methanol). 2.2 g of a pasty oil are obtained (84% yield).

1. temperatureThe mixture is refluxed
2. temperatureAfter cooling
3. customthe acetone is partially evaporated off
4. additionWater is added to the residue
5. extractionthe mixture is extracted with dichloromethane
6. extractionThe organic phase is extracted with 1N hydrochloric acid
7. customThe acidic aqueous phase obtained
8. extractionextracted with dichloromethane
9. washThe extract is washed with water and with brine
10. dry with materialdried over anhydrous sodium sulfate
11. customevaporated under reduced pressure
12. customThe residue obtained
13. filtrationis filtered on silica gel (solvent: 95/5 (v/v) dichloromethane/methanol)