反応 #2298665

反応方程式

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

K2CO3

4-(3-bromopropoxy)-3-methoxybenzonitrile

→

4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperdinyl]propoxy]-3-methoxybenzonitrile

収率 68.2%

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux for 3 hr
3. 3
   その他At the end of the reaction
4. 4
   その他the solvent was removed on a rotary evaporator
5. 5
   抽出The organic material was extracted into dichloromethane (250 ml)
6. 6
   ろ過the inorganics were filtered off
7. 7
   濃縮The dichloromethane solution was concentrated to a crude oil
8. 8
   その他The purification
9. 9
   洗浄was done by flash chromatography over a silica gel column (SiO2, 55 gm; eluted with dichloromethane, 600 ml; 1% methanol in dichloromethane, 600 ml)
10. 10
    その他The material thus obtained
11. 11
    その他was crystallized from a small amount of dichloromethane
12. 12
    その他Recrystallization from ethanol (25 ml)

実験手順

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.0 g, 13.6 mmoles), K2CO3 (2.8 g), 4-(3-bromopropoxy)-3-methoxybenzonitrile (4.0 gm, 14.8 mmoles) in acetonitrile (70 ml) was heated at reflux for 3 hr. At the end of the reaction, the solvent was removed on a rotary evaporator. The organic material was extracted into dichloromethane (250 ml) and the inorganics were filtered off. The dichloromethane solution was concentrated to a crude oil. The purification was done by flash chromatography over a silica gel column (SiO2, 55 gm; eluted with dichloromethane, 600 ml; 1% methanol in dichloromethane, 600 ml). The material thus obtained was crystallized from a small amount of dichloromethane. Recrystallization from ethanol (25 ml) provided 3.8 gm (68%) of 4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperdinyl]propoxy]-3-methoxybenzonitrile as white crystals, m.p.=107°-108° C.

出典