Réaction #2300

Équation de réaction

methyl 4-chloroacetylphenylacetate

1-(4-pyridyl)piperazine

→

title compound

Methyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]-phenylacetate

Solvants

acetonitrile

acetonitrile

Conditions de réaction

Traitement

1. 1
   AutreThe supernatent was decanted from the solid
2. 2
   Autreformed
3. 3
   Concentrationconcentrated in vacuo
4. 4
   Autrepurified by flash chromatography on neutral alumina
5. 5
   Lavageeluting with dichloromethane

Mode opératoire

A solution of methyl 4-chloroacetylphenylacetate (260 mg) in acetonitrile (4 ml) was added dropwise over 15 minutes to a stirred solution of 1-(4-pyridyl)piperazine (375 mg) in acetonitrile (10 ml) and the mixture stirred overnight. The supernatent was decanted from the solid formed, concentrated in vacuo and purified by flash chromatography on neutral alumina, eluting with dichloromethane then 0.25% v/v methanol/dichloromethane and finally 0.5% v/v methanol dichloromethane. Concentration of the fractions in vacuo gave the title compound, 96 mg, as a white crystalline solid: m.p. 127°-129° C.; NMR (d6 DMSO) δ 8.15(2H,d), 7.98(2H,d), 7.41(2H,d), 6.81(2H,d), 3.91(2H,s), 3.78(2H,s), 3.53(3H,s), 3.33(4H,t), 2.64(4H,t); m/e 354(M+H )+ ; calculated for C20H23N3O3 : C, 68.0; H, 6.6; N, 11.9. found: C, 68.2; H, 6.6; N, 11.9%.

Source