反应详情

温度

65 °C

To a solution of tert-butyl 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexylcarbamate (24.6 g, 56.1 mmol) in ethanol (100 mL) was added 2.7 M HCl in ethanol (150 mL). The solution was heated at 65° C. for 4 h, the was allowed to cool to rt overnight. A light brown precipitate was isolated by filtration and washed with ethanol. The precipitate was dissolved in water (100 mL) and NaOH was added until the pH=14. The mixture was extracted with dichloromethane (3×200 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated to an oil that was dissolved in ethanol (100 mL). To the ethanol solution was added 2.7 M HCl in ethanol (18.7 mL). A pale tan solid crashed out of solution and was isolated by filtration and dried. The solid was dissolved in water (100 mL) and NaOH was added until the pH=14. The mixture was extracted with dichloromethane (3×200 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated to yield 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanamine as a light yellow oil (15.1 g, 79%).

1. temperatureto cool to rt overnight
2. customA light brown precipitate was isolated by filtration
3. washwashed with ethanol
4. dissolutionThe precipitate was dissolved in water (100 mL)
5. additionNaOH was added until the pH=14
6. extractionThe mixture was extracted with dichloromethane (3×200 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated to an oil that
10. dissolutionwas dissolved in ethanol (100 mL)
11. additionTo the ethanol solution was added 2.7 M HCl in ethanol (18.7 mL)
12. customwas isolated by filtration
13. customdried
14. dissolutionThe solid was dissolved in water (100 mL)
15. additionNaOH was added until the pH=14
16. extractionThe mixture was extracted with dichloromethane (3×200 mL)
17. dry with materialdried over Na2SO4
18. filtrationfiltered
19. concentrationconcentrated