反応 #83981

反応方程式

fumaric acid

N-(2,3-epoxypropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine

1,2,3,4-tetrahydroquinoline

→

white crystals

N-[3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl)-2-hydroxy-1-propyl]-1,2,3,4-tetrahydroquinoline hemifumarate

溶媒

isopropyl alcohol

ethanol

反応条件

後処理

1. 1
   温度at reflux for 6 hours
2. 2
   温度The solution was cooled
3. 3
   その他the solvent was removed on a rotary evaporator
4. 4
   その他The crude solid was purified by flash chromatography over a silica gel column (SiO2, 40 g, eluted with methylene chloride DCM, and 1-3% MeOH in DCM)
5. 5
   その他The product thus purified
6. 6
   workup.DISSOLUTIONThis material was dissolved in ethanol
7. 7
   その他The solids collected
8. 8
   その他were recrystallized again from ethanol (50 ml)

実験手順

A stirred mixture of N-(2,3-epoxypropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (2.41 g, 8.73 mmol), 1,2,3,4-tetrahydroquinoline (1.33 g, 10 mmol, in isopropyl alcohol (50 ml) was heated at reflux for 6 hours. The solution was cooled and the solvent was removed on a rotary evaporator. The crude solid was purified by flash chromatography over a silica gel column (SiO2, 40 g, eluted with methylene chloride DCM, and 1-3% MeOH in DCM). The product thus purified weighed 2.0 g. This material was dissolved in ethanol and was treated with a solution of fumaric acid (567 mg, 1.0 eq) in ethanol. The solids collected were recrystallized again from ethanol (50 ml) to yield 1.0 g of white crystals, as a hemifumarate, m.p. 170°-171 ° C.

出典