반응 #2169653

반응 방정식

(S)-7-[3-[[(2,3-Dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one hydrochloride

iodoethane

diisopropylethylamine

→

title compound

수율 43.8%

(S)-7-[3-[[(2,3-Dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-yl)methyl]ethylamino]propoxy]-2H-1-benzopyran-2-one

수율 43.8%

용매

DMF

반응 조건

후처리

1. 1
   기타The solvent was then removed in vacuum
2. 2
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane
3. 3
   세척washed with an equal volume of aqueous saturated sodium bicarbonate
4. 4
   추출The aqueous portion was back-extracted with dichloromethane
5. 5
   세척the combined organic portions were washed with water
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated under reduced pressure
9. 9
   기타The residue was chromatographed on a silica gel column
10. 10
    농축concentrated in vacuum
11. 11
    workup.DISSOLUTIONthe residue redissolved in methanol
12. 12
    기타acidified with 4N HCl/isopropanol to pH<3 in an ice bath
13. 13
    workup.ADDITIONThe mixture was diluted with isopropanol
14. 14
    기타to precipitate a white solid, which
15. 15
    기타was recrystallized from methanol

실험 절차

(S)-7-[3-[[(2,3-Dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one hydrochloride (0.60 g, 1.3 mmole), iodoethane (0.16 ml, 2.0 mmole) and diisopropylethylamine (2.26 ml, 13.0 mmole) were combined in 50 ml of DMF and heated at 60° C. for 2 days under a nitrogen atmosphere. The solvent was then removed in vacuum and the residue was dissolved in dichloromethane and washed with an equal volume of aqueous saturated sodium bicarbonate. The aqueous portion was back-extracted with dichloromethane and the combined organic portions were washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using dichloromethane as eluant. The product-containing fractions were combined and concentrated in vacuum, and the residue redissolved in methanol and acidified with 4N HCl/isopropanol to pH<3 in an ice bath. The mixture was diluted with isopropanol to precipitate a white solid, which was recrystallized from methanol to give 0.25 g of the title compound as the monohydrochloride, m.p. 209° C.

출처