Reacción #41208

Ecuación de reacción

compound

3-[4-(4-Hydroxy-phenyl)-piperazin-1-yl]-butyric acid methyl ester

K2CO3

3-bromopropyne

→

title compound

Rendimiento 39.7%

3-[4-(4-Prop-2-ynyloxy-phenyl)-piperazin-1-yl]-propionic acid methyl ester

Rendimiento 39.7%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropartitioned between water and ethyl acetate
2. 2
   Lavadowashed with brine
3. 3
   Secadodried over anhydrous Na2SO4
4. 4
   Otroevaporated under vacuum
5. 5
   Otroto give a brown oil
6. 6
   OtroThe crude product was purified by silica gel flash chromatography (30% ethyl acetate in hexane)

Procedimiento

To a mixture of the compound from step 1 (278 mg, 1.0 mmol) and K2CO3 (152 mg, 1.1 mmol) in DMF (5 mL) was added 3-bromopropyne (130 mg, 1.1 mmol) dropwise at rt. The reaction mixture was stirred at rt overnight and then partitioned between water and ethyl acetate. The organic payers were combined and washed with brine, dried over anhydrous Na2SO4 and evaporated under vacuum to give a brown oil. The crude product was purified by silica gel flash chromatography (30% ethyl acetate in hexane) to furnish the title compound (120 mg, 38%) as a light yellow solid; MS; m/z 317 (M+H).

Fuente