반응 #5667

반응 방정식

6-[3-[[(6,7-Dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-yl)methyl]amino]propoxy]chromen-4-one hydrochloride

HCl IPA

→

title compound

수율 56.3%

N-[3-(Chroman-6-yloxy)-propyl]-6,7-dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-methanamine

수율 56.3%

용매

methanol

반응 조건

후처리

1. 1
   기타4 psi of hydrogen was absorbed
2. 2
   workup.ADDITIONWater (10 ml) was added
3. 3
   workup.DISSOLUTIONto dissolved the resulting mixture
4. 4
   기타the catalyst was removed by filteration
5. 5
   농축The filtrate was concentrated
6. 6
   workup.ADDITIONthe residue was treated with saturated aqueous sodium bicarbonate
7. 7
   추출extracted with dichloromethane
8. 8
   세척The extract was washed with water
9. 9
   건조dried over anhydrous magnesium sulfate
10. 10
    여과filtered
11. 11
    농축concentrated
12. 12
    기타The crude product was chromatographed on a silica gel column
13. 13
    농축concentrated
14. 14
    workup.DISSOLUTIONdissolved in methanol
15. 15
    기타The resulting precipitate was collected on a Buchner funnel
16. 16
    기타recrystallized from methanol

실험 절차

6-[3-[[(6,7-Dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-yl)methyl]amino]propoxy]chromen-4-one hydrochloride (0.9 g, 2.0 mmole), prepared in Example 5 above, was dissolved in 50 ml of methanol and 4N HCl/IPA (12.5 ml, 50 mmole) and 10% Palladium on Carbon (0.2 g) were added. The mixture was hydrogenated on a Parr apparatus for 24 hours and 4 psi of hydrogen was absorbed. Water (10 ml) was added to dissolved the resulting mixture and the catalyst was removed by filteration. The filtrate was concentrated, and the residue was treated with saturated aqueous sodium bicarbonate and extracted with dichloromethane. The extract was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude product was chromatographed on a silica gel column using 5% methanol in dichloromethane as an eluent. The product-containing fractions (Rf=0.47 on silica gel with 5% chloroform/methanol) were combined, concentrated, dissolved in methanol and acidified with 4N HCl/IPA until the solution was 3 in pH. The resulting precipitate was collected on a Buchner funnel and recrystallized from methanol to give 0.45 g of title compound as a white solid hydrochloride, m.p. 217°-218° C.

출처