反应详情

To a solution of 3-(3,4-dimethoxyphenyl)prop-2-en-1-ol (270 mg) in dimethyl-sulfoxyde (4 mL) are added successively powdered potassium hydroxyde (175 mg 85% wt) and, portionwise, 1-(3-chloropropyl)piperidine, hydrochloride (250 mg). The mixture is stirred overnight at room temperature, then hydrolysed with water (80 mL). The solution is extracted twice with ethyl acetate (20 mL). The combined extracts are washed twice with water (10 mL), dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel with a gradient dichloromethane/methanol from 98/2 to 90/10. Fractions containing the expected product are pooled, concentrated under reduced pressure, dissolved in 10 mL of dichloromethane, filtered over Millipore membrane and concentrated under reduced pressure. The base thus obtained is dissolved in 2 mL of ethanol and 100 μL of diethyl oxide. A solution of 88 mg of oxalic acid in 2 mL of ethanol is added. The precipitate that appears is filtered, washed with diethyl oxide and dried under reduced pressure at a temperature close to 40 C to give 185 mg of trans-1-{3-[3-(3,4-dimethoxyphenyl)allyloxy]propyl}piperidine, oxalate as a white powder melting at 111-112° C.

1. extractionThe solution is extracted twice with ethyl acetate (20 mL)
2. washThe combined extracts are washed twice with water (10 mL)
3. dry with materialdried over magnesium sulphate
4. concentrationconcentrated under reduced pressure
5. custompurified by chromatography over silica gel with a gradient dichloromethane/methanol from 98/2 to 90/10
6. additionFractions containing the expected product
7. concentrationconcentrated under reduced pressure
8. dissolutiondissolved in 10 mL of dichloromethane
9. filtrationfiltered over Millipore membrane
10. concentrationconcentrated under reduced pressure
11. customThe base thus obtained
12. filtrationThe precipitate that appears is filtered
13. washwashed with diethyl oxide
14. customdried under reduced pressure at a temperature
15. customclose to 40 C