反应详情

Trifluoroacetic acid (37.5 ml) was added to a solution of ethyl 3-methoxy-4-(1-methylpiperidin-4-ylmethoxy)benzoate (30.6 g, 89 mmol) in dichloromethane (75 ml) at 0–5° C. before dropwise addition of a solution of fuming nitric acid (7.42 ml, 178 mmol) in dichloromethane (15 ml) over 15 minutes. The reaction was stirred at ambient temperature for 2 hours, the volatiles were removed in vacuo and the residue was dissolved in dichloromethane (50 ml). The solution was cooled to 0–5° C., diethyl ether was added (50 ml) and the resultant precipitate was collected by suction filtration, and dried in vacuo. The solid was taken up in dichloromethane (500 ml), 3.0N hydrogen chloride in diethyl ether (30 ml) was added followed by diethyl ether (500 ml) which cause precipitation of a solid. Collection of the solid by suction filtration followed by drying in vacuo yielded ethyl 3-methoxy-4-(1-methylpiperidin-4-ylmethoxy)-6-nitrobenzoate (28.4 g, 82% yield) as a white solid:

1. customthe volatiles were removed in vacuo
2. dissolutionthe residue was dissolved in dichloromethane (50 ml)
3. temperatureThe solution was cooled to 0–5° C.
4. additiondiethyl ether was added (50 ml)
5. filtrationthe resultant precipitate was collected by suction filtration
6. customdried in vacuo
7. addition3.0N hydrogen chloride in diethyl ether (30 ml) was added
8. customprecipitation of a solid
9. customCollection of the solid
10. filtrationby suction filtration
11. customby drying in vacuo