反应详情

A solution of 1,4-benzodioxan-2-carbonyl chloride (0.75 g) in chloroform (10 ml) was added dropwise to a stirred solution of 4-amino-6,7-dimethoxy-2-(piperazin-1-yl)quinoline (1.0 g) in chloroform (50 ml) with triethylamine (1.06 g) at 5°-10°. The reaction was stirred at 5°-10° for one hour, then allowed to attain room temperature and stirred overnight. The mixture was then evaporated in vacuo and the residue partitioned between chloroform (50 ml) and sodium carbonate solution (10%, 50 ml). The chloroform layer was separated, the aqueous phase extracted with chloroform (2×50 ml), the extracts combined, washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was then taken up in chloroform and chromatographed on silica (Merck 9385, 60 g) eluting with chloroform/methanol (100:0→97:3). A solution of the purified product in chloroform was treated with ethereal hydrogen chloride, evaporated in vacuo and the residue recrystallised from isopropanol to give 4-amino-2-[ 4-(1,4-benzodioxan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinoline hydrochloride hydrate (0.28 g), m.p. 201°.

1. customto attain room temperature
2. stirringstirred overnight
3. customThe mixture was then evaporated in vacuo
4. customthe residue partitioned between chloroform (50 ml) and sodium carbonate solution (10%, 50 ml)
5. customThe chloroform layer was separated
6. extractionthe aqueous phase extracted with chloroform (2×50 ml)
7. washwashed with brine
8. dry with materialdried (Na2SO4)
9. customevaporated in vacuo
10. customchromatographed on silica (Merck 9385, 60 g)
11. washeluting with chloroform/methanol (100:0→97:3)
12. additionA solution of the purified product in chloroform was treated with ethereal hydrogen chloride
13. customevaporated in vacuo
14. customthe residue recrystallised from isopropanol