反应详情

A sample of 44.4 g. of product from Step 3, 3-[N'-(3-hydroxypropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium bromide, is dissolved in 500 ml. of water and acidified to pH 2 with concentrated hydrochloric acid. The solution is passed through a column of Dowex 1-X2 chloride form ion exchange resin and the eluant is evaporated under reduced pressure. The residual viscous oil is dried in vacuo and treated with thionyl chloride (25 ml.) added dropwise with stirring during one hour. The solution is heated at 50° for 1.5 hours and then evaporated under reduced pressure. The residue is washed with ether (2×200 ml.) and dried in vacuo. The crude product is dissolved in 100 ml. of water and 0.5 g. of charcoal is added. The mixture is heated to boiling and stirred while hot for one hour. After being filtered through Celite, the filtrate is evaporated under reduced pressure. To the residue is added 40 ml. of isopropanol, which is evaporated. Another 40 ml. of isopropanol is added and the evaporation is repeated until 10 ml. of isopropanol remains. At this point, 100 ml. acetone is added and the product is crystallized. The solid is chopped to a fine powder and collected by suction filtration. The solid is washed with 3:1/acetone: isopropanol (2×90 ml.)and acetone (90ml.). The product is recrystallized from 1:2/isopropanol:acetone to give 30 g. of desired product. Further purification provided the analytic sample.

1. customthe eluant is evaporated under reduced pressure
2. customThe residual viscous oil is dried in vacuo
3. additiontreated with thionyl chloride (25 ml.)
4. additionadded dropwise
5. temperatureThe solution is heated at 50° for 1.5 hours
6. customevaporated under reduced pressure
7. washThe residue is washed with ether (2×200 ml.)
8. customdried in vacuo
9. dissolutionThe crude product is dissolved in 100 ml
10. additionof charcoal is added
11. temperatureThe mixture is heated
12. stirringstirred while hot for one hour
13. filtrationAfter being filtered through Celite
14. customthe filtrate is evaporated under reduced pressure
15. additionTo the residue is added 40 ml
16. customof isopropanol, which is evaporated
17. additionof isopropanol is added
18. customthe evaporation
19. additionacetone is added
20. customthe product is crystallized
21. filtrationcollected by suction filtration
22. washThe solid is washed with 3:1/acetone
23. customThe product is recrystallized from 1:2/isopropanol
24. customacetone to give 30 g