反応 #83853

反応方程式

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

K2CO3

1-[3-(3-chloropropoxy)-4-methoxy-phenyl]phenylmethanone

→

1-[3-[3-[4-(6- fluoro-1,2-benzisoxa zol-3-yl)-1-piperidinyl]propoxy]-4-methoxyphenyl]-phenylmethanone

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度at reflux for 4 hours
3. 3
   その他At the end of the reaction
4. 4
   その他the solvent was evaporated
5. 5
   その他the residue was partitioned between water (150 ml) and dichloromethane (400 ml)
6. 6
   洗浄The dichloromethane solution was washed with water and brine (100 ml)
7. 7
   乾燥dried over MgSO4
8. 8
   濃縮concentrated to an oil
9. 9
   その他The purification
10. 10
    洗浄was done by flash chromatography over a silica gel column (SiO2, 40 g; eluted with dichloromethane, 300 ml; 1% methanol in dichloromethane, 850 ml)
11. 11
    その他The material thus obtained as a colorless oil
12. 12
    その他Recrystallization from ethanol (150 ml)

実験手順

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2 benzisoxazole (2.01 g; 9.13 mmol), K2CO3 (2.0 g), and 1-[3-(3-chloropropoxy)-4-methoxy-phenyl]phenylmethanone (3.93 g; 11.3 mmol) and acetonitrile (50 ml) was heated at reflux for 4 hours. At the end of the reaction, the solvent was evaporated and the residue was partitioned between water (150 ml) and dichloromethane (400 ml). The dichloromethane solution was washed with water and brine (100 ml), dried over MgSO4, then concentrated to an oil. The purification was done by flash chromatography over a silica gel column (SiO2, 40 g; eluted with dichloromethane, 300 ml; 1% methanol in dichloromethane, 850 ml). The material thus obtained as a colorless oil solidified on standing. Recrystallization from ethanol (150 ml) gave 1-[3-[3-[4-(6- fluoro-1,2-benzisoxa zol-3-yl)-1-piperidinyl]propoxy]-4-methoxyphenyl]-phenylmethanone as white crystals, 3.07 g (63%), m.p.=140°-141° C.

出典