반응 #5668

반응 방정식

2,3-Dihydro-7-methoxy-1,4-benzodioxin-2-methanamine hydrochloride

7-(3-bromopropoxy)chromen-4-one

diisopropylethylamine

→

title compound

수율 4.4%

7-[3-[(7-Methoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)amino]propoxy]chromen-4-one

수율 4.4%

용매

DMF

반응 조건

후처리

1. 1
   기타The solvent was then removed
2. 2
   세척The mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated in vacuum
6. 6
   기타The residue was chromatographed on a silica gel column
7. 7
   workup.ADDITIONThe fractions containing material with Rf=0.59 on silica gel tlc (chloroform/methanol/ammonia=95/5/1)
8. 8
   농축concentrated
9. 9
   workup.DISSOLUTIONthe residue was dissolved in 50% methanol/dichloromethane
10. 10
    workup.ADDITIONThe mixture was then treated with 4N isopropanolic HCl until the solution
11. 11
    기타crystallized
12. 12
    기타by triturating with ether
13. 13
    기타Two further recrystallizations

실험 절차

2,3-Dihydro-7-methoxy-1,4-benzodioxin-2-methanamine hydrochloride (4.0 g, 17 mmole), 7-(3-bromopropoxy)chromen-4-one (4.9 g, 17 mmole) and diisopropylethylamine (15.1 ml, 87 mmole) were combined in 150 ml of DMF and heated at 80° C. for 24 hours under a nitrogen atmosphere. The solvent was then removed and replaced with dichloromethane. The mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuum. The residue was chromatographed on a silica gel column using first dichloromethane and then 5% methanolic dichloromethane as eluents. The fractions containing material with Rf=0.59 on silica gel tlc (chloroform/methanol/ammonia=95/5/1) were combined, concentrated, and the residue was dissolved in 50% methanol/dichloromethane. The mixture was then treated with 4N isopropanolic HCl until the solution was 3 in pH and crystallized by triturating with ether. Two further recrystallizations gave 0.3 g of title compound as a yellow solid hydrochloride, quarter hydrate, m.p. 155°-157° C.

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