反応 #2298672

反応方程式

acetonitrile

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

K2CO3

1-[4-(3-chloropropoxy)-3-(methylamino)phenyl] ethanone

→

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

収率 47.9%

溶媒

water

methanol methylene chloride

反応条件

後処理

1. 1
   温度at reflux under nitrogen for 23 hours
2. 2
   抽出the aqueous mixture was extracted with ethyl acetate
3. 3
   抽出The ethyl acetate extract
4. 4
   洗浄was washed twice with water
5. 5
   乾燥dried with MgSO4
6. 6
   濃縮was concentrated
7. 7
   その他to yield 4.8 g of a damp, brown solid
8. 8
   その他Concentration of appropriate fractions afforded 2.4 g
9. 9
   その他Recrystallization from ethanol

実験手順

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2- benzisoxazole (2.3 g, 0.0103 mol), K2CO3 (1,4 g, 0.0103 mol), 1-[4-(3-chloropropoxy)-3-(methylamino)phenyl] ethanone (2.5 g 0.0103 mol). KI (0.10 g), and acetonitrile (100 ml) was stirred at reflux under nitrogen for 23 hours. The reaction was cooled to ambient temperature, poured into water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate extract was washed twice with water, dried with MgSO4 and was concentrated to yield 4.8 g of a damp, brown solid. The compound was isolated by preparative HPLC (Waters Associates prep LC/System 500, utilizing 2 silica gel columns and 4% methanol-methylene chloride as eluent). Concentration of appropriate fractions afforded 2.4 g. Recrystallization from ethanol gave 2.1 g of 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl] propoxy]-3-(methylamino)phenyl]ethanone as a beige solid, m.p.=151°-153° C.

出典