反应详情

N-Methyl-4-chlorobenzylamine (1.40 g., 9.0 mmol) and 1-chloro-3-methyl-4-isoquinoline acetic acid (770 mg., 3.0 mmol), prepared as in Example 8, were refluxed in 20 ml. p-dioxane for 16 hr. The cooled reaction mixture was partitioned between 200 ml ether and 50 ml 1 N sodium hydroxide. The ether rafinate was extracted with 2×30 ml 1 N sodium hydroxide. The combined basic phases were acidified to pH 6.5 with 6 N hydrochloric acid and extracted with 3×75 ml ethyl acetate. This organic phase was dried over magnesium sulfate, filtered, and vacuum evaporated to an oily residue. Chromatography of this on silica gel eluted with ethyl acetate gave an oil. The title compound was prepared from this oil by treatment with hydrochloric acid gas in ether, filtrate, and drying in vacuo; 52 mg. (4%), m/e 354.

1. temperaturewere refluxed in 20 ml
2. customThe cooled reaction mixture
3. customwas partitioned between 200 ml ether and 50 ml 1 N sodium hydroxide
4. extractionThe ether rafinate was extracted with 2×30 ml 1 N sodium hydroxide
5. extractionextracted with 3×75 ml ethyl acetate
6. dry with materialThis organic phase was dried over magnesium sulfate
7. filtrationfiltered
8. customvacuum evaporated to an oily residue
9. washChromatography of this on silica gel eluted with ethyl acetate
10. customgave an oil
11. customdrying in vacuo