反応 #2006487

反応方程式

compound 26

4-(2-Hydroxy-ethyl)-piperidin-4-ol

triethylamine

4-fluoro-2-trifluoromethylbenzonitrile

→

desired compound 27a

収率 68.0%

4-[4-Hydroxy-4-(2-hydroxy-ethyl)-piperidin-1-yl]-2-trifluoromethyl-benzonitrile

収率 68.0%

溶媒

dimethylformamide

water

反応条件

後処理

1. 1
   温度The solution was cooled at room temperature
2. 2
   抽出extracted with diethyl ether (3×25 mL)
3. 3
   洗浄washed with brine
4. 4
   乾燥finally dried over magnesium sulphate
5. 5
   その他Purification of the resulting crude product by flash chromatography

実験手順

To a solution of compound 26 (517 mg, 3.25 mmol) in anhydrous dimethylformamide (15 mL) under argon were added triethylamine (1.32 g, 13.0 mmol) and 4-fluoro-2-trifluoromethylbenzonitrile (1.80 g, 9.52 mmol). The solution was stirred at 80° C. for 4 hrs. The solution was cooled at room temperature and poured in water (100 mL), extracted with diethyl ether (3×25 mL), washed with brine and finally dried over magnesium sulphate. Purification of the resulting crude product by flash chromatography using ethyl acetate/hexane (7:3) as an eluant gave the desired compound 27a (687 mg, 68%). 1H NMR (400 MHz, Acetone-d6) δ: 1.74 (m, 6H), 3.45 (m, 2H), 3.85 (m, 4H), 7.24 (dd, 1H, J1=6.4 Hz, J2=2.5 Hz), 7.32 (d, 1H, J=2.4 Hz), 7.72 (d, 1H, J=8.8 Hz).

出典