Reaction #2271668

Reaction equation

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

K2CO3

1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone

dimethylformamide

→

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

Yield 58.6%

Solvents

water

Conditions

Workup

1. 1
   Extractionthe aqueous mixture was extracted with ethyl acetate
2. 2
   WashThe ethyl acetate was washed (water)
3. 3
   Dryingdried (MgSO4)
4. 4
   Concentrationconcentrated
5. 5
   Otherto afford a moist solid
6. 6
   OtherRecrystallization (twice) from ethyl alcohol

Procedure

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2 benzisoxazole hydrochloride (5.1 g, 20 mmol). K2CO3 (5.2 g, 40 mmol), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (5.3 g, 22 mmol), and dimethylformamide (60 ml) was heated at 90° C. for 16 hours. The reaction was poured into water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate was washed (water), dried (MgSO4) and concentrated to afford a moist solid. Recrystallization (twice) from ethyl alcohol afforded 5.0 g (58%) of 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]-ethanone as a beige solid, m.p.=118°-120° C.

Source