反応 #82483

反応方程式

1-(2-methoxyphenyl)-4-[1-hydroxy-1(3,5-dimethylpyridin-2-yl)-cyclohex-4-yl]piperazine

imidazole

→

title compound

収率 61.8%

1-(2-Methoxyphenyl)-4-[1-(3,5-dimethylpyridin-2-yl)-cyclohex-1-en-4-yl]piperazine

収率 61.8%

溶媒

THF

反応条件

後処理

1. 1
   温度at reflux
2. 2
   温度Heating
3. 3
   その他when the solvent was evaporated in vacuo
4. 4
   温度The mixture was heated
5. 5
   温度under reflux overnight
6. 6
   温度when cool
7. 7
   workup.ADDITIONadded to dilute NaOH (aq)
8. 8
   抽出extracted by ether (3×50 ml)
9. 9
   洗浄The combined organic extracts were washed with brine (50 ml) and water (50 ml)
10. 10
    乾燥dried over magnesium sulphate
11. 11
    その他evaporated to dryness
12. 12
    その他The crude product was chromatographed (SiO2, 2% methanol in dichloromethane)

実験手順

Methyloxalyl chloride (0.35 ml) was added to a mixture of 1-(2-methoxyphenyl)-4-[1-hydroxy-1(3,5-dimethylpyridin-2-yl)-cyclohex-4-yl]piperazine (0.7 g, 1.8 mmol) and imidazole (0.25 g) in THF (15 ml) at reflux. Heating was continued overnight when the solvent was evaporated in vacuo and replaced with toluene (15 ml). The mixture was heated under reflux overnight, then, when cool, added to dilute NaOH (aq) and extracted by ether (3×50 ml). The combined organic extracts were washed with brine (50 ml) and water (50 ml), dried over magnesium sulphate and evaporated to dryness. The crude product was chromatographed (SiO2, 2% methanol in dichloromethane) giving the title compound (0.42 g) which was recrystallised from hexane then treated with ethanolic HCl to give the title compound as the trihydrochloride 2.25 hydrate, m.p. 235°-236° C.

出典