反応 #163262

反応方程式

4′-fluoroacetophenone

2-(piperidin-4-yl)-acetic acid ethyl ester

DMSO

→

title compound

[1-(4-Acetyl-phenyl)-piperidin-4-yl]-acetic acid ethyl ester

溶媒

ether

反応条件

後処理

1. 1
   その他The homogeneous reaction
2. 2
   その他The cooled reaction
3. 3
   洗浄washed sequentially with saturated ammonium chloride, water, and brine
4. 4
   乾燥The organic extracts were then dried over sodium sulphate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated in vacuo
7. 7
   その他Purification by flash chromatography (10-40% EtOAc in hexanes)

実験手順

A microwave vial was charged with 4′-fluoroacetophenone (1.2 Ml, 10.4 mmol, 1.0 equiv) and 2-(piperidin-4-yl)-acetic acid ethyl ester (3.5 g, 20.7 mmol, 2.0 equiv) in 20 Ml DMSO. The homogeneous reaction was heated to 150° C. for 20 min. The cooled reaction was then diluted with ether and washed sequentially with saturated ammonium chloride, water, and brine. The organic extracts were then dried over sodium sulphate, filtered, and concentrated in vacuo. Purification by flash chromatography (10-40% EtOAc in hexanes) afforded the title compound: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.32 (t, J=7.07 Hz, 3H) 1.47 (d, J=12.13 Hz, 2H) 1.62 (br.s., 1H) 1.90 (d, J=12.63 Hz, 2H) 2.04-2.15 (m, J=11.18, 11.18, 7.45, 7.45, 3.79, 3.66 Hz, 1H) 2.33 (d, J=7.07 Hz, 2H) 2.57 (s, 3H) 2.97 (td, J=12.57, 2.15 Hz, 2H) 3.93 (d, J=12.88 Hz, 2H) 4.20 (q, J=7.07 Hz, 2H) 6.96 (d, J=6.82 Hz, 2H) 7.92 (d, J=9.09 Hz, 2H); (M+H)+290.1.

出典