تفاعل #5667

معادلة التفاعل

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

المردود 56.3%

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

المردود 56.3%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   أخرى4 psi of hydrogen was absorbed
2. 2
   workup.ADDITIONWater (10 ml) was added
3. 3
   workup.DISSOLUTIONto dissolved the resulting mixture
4. 4
   أخرىthe catalyst was removed by filteration
5. 5
   تركيزThe filtrate was concentrated
6. 6
   workup.ADDITIONthe residue was treated with saturated aqueous sodium bicarbonate
7. 7
   استخلاصextracted with dichloromethane
8. 8
   غسيلThe extract was washed with water
9. 9
   تجفيفdried over anhydrous magnesium sulfate
10. 10
    ترشيحfiltered
11. 11
    تركيزconcentrated
12. 12
    أخرىThe crude product was chromatographed on a silica gel column
13. 13
    تركيزconcentrated
14. 14
    workup.DISSOLUTIONdissolved in methanol
15. 15
    أخرىThe resulting precipitate was collected on a Buchner funnel
16. 16
    أخرىrecrystallized from methanol

الإجراء التجريبي

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.

المصدر