Reacción #163262

Ecuación de reacción

4′-fluoroacetophenone

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

DMSO

→

title compound

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

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe homogeneous reaction
2. 2
   OtroThe cooled reaction
3. 3
   Lavadowashed sequentially with saturated ammonium chloride, water, and brine
4. 4
   SecadoThe organic extracts were then dried over sodium sulphate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroPurification by flash chromatography (10-40% EtOAc in hexanes)

Procedimiento

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.

Fuente