反応 #2298660

反応方程式

6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride

K2CO3

1-[2-(3-bromopropoxy)-5-methylphenyl]ethanone

→

1-[2-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-5-methylphenyl]ethanone

収率 46.2%

溶媒

dimethylformamide

acetonitrile

反応条件

後処理

1. 1
   その他At the end of the reaction
2. 2
   濃縮the solvent was concentrated
3. 3
   抽出the mixture was extracted into dichloromethane (300 ml)
4. 4
   洗浄The organic solution was washed with water and brine
5. 5
   乾燥dried over MgSO4
6. 6
   濃縮concentrated down to a crude oil
7. 7
   その他The purification
8. 8
   洗浄was done by flash chromatography over a silica gel column (SiO2, 60 g, eluted with 1% CH3OH:dichloromethane: 1.2 l; 3% CH3OH:dichloromethane: 600 ml)
9. 9
   その他The material thus obtained
10. 10
    その他was crystallized from a small volume of ether and hexane

実験手順

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (2.87 g, 11.23 mmoles), K2CO3 (2.5 g), 1-[2-(3-bromopropoxy)-5-methylphenyl]ethanone (3.74 g, 13.8 mmoles) in dimethylformamide (10 ml) and acetonitrile (50 ml) was heated at 95° C. for 6 hr. At the end of the reaction, the solvent was concentrated and the mixture was extracted into dichloromethane (300 ml). The organic solution was washed with water and brine, dried over MgSO4, then concentrated down to a crude oil. The purification was done by flash chromatography over a silica gel column (SiO2, 60 g, eluted with 1% CH3OH:dichloromethane: 1.2 l; 3% CH3OH:dichloromethane: 600 ml). The material thus obtained was crystallized from a small volume of ether and hexane to provide 2.13 gm (46%) of off-white 1-[2-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-5-methylphenyl]ethanone, m.p.=92°-93° C.

出典