반응 #163262

반응 방정식

4′-fluoroacetophenone

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

DMSO

→

title compound

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

용매

ether

반응 조건

후처리

1. 1
   기타The homogeneous reaction
2. 2
   기타The cooled reaction
3. 3
   세척washed sequentially with saturated ammonium chloride, water, and brine
4. 4
   건조The organic extracts were then dried over sodium sulphate
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타Purification by flash chromatography (10-40% EtOAc in hexanes)

실험 절차

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.

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