反応 #5668

反応方程式

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

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

diisopropylethylamine

→

title compound

収率 4.4%

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

収率 4.4%

溶媒

DMF

反応条件

後処理

1. 1
   その他The solvent was then removed
2. 2
   洗浄The mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride
3. 3
   乾燥dried over anhydrous magnesium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuum
6. 6
   その他The 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
   濃縮concentrated
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
    その他crystallized
12. 12
    その他by triturating with ether
13. 13
    その他Two further recrystallizations

実験手順

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.

出典