반응 #83871

반응 방정식

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

K2CO3

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

acetonitrile

→

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

수율 47.9%

용매

water

methanol methylene chloride

반응 조건

후처리

1. 1
   온도at reflux under nitrogen for 23 hours
2. 2
   추출the aqueous mixture was extracted with ethyl acetate
3. 3
   추출The ethyl acetate extract
4. 4
   세척was washed twice with water
5. 5
   건조dried with MgSO4
6. 6
   농축was concentrated
7. 7
   기타to yield 4.8 g of a damp, brown solid
8. 8
   기타Concentration of appropriate fractions afforded 2.4 g
9. 9
   기타Recrystallization from ethanol

실험 절차

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.3 g, 10.3 mmol), K2CO3 (1.4 g, 10.3 mmol), 1-[4-(3-chloropropoxy)-3-(methylamino)phenyl]ethanone (2.5 g, 10.3 mmol), 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.

출처