反应 #2315

反应方程式

iso-Propyl 4-bromoacetylphenoxyacetate

1-(4-pyridyl)piperazine

→

title compound

iso-Propyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]-phenoxyacetate

溶剂

acetonitrile

反应条件

后处理

1. 1
   其他overnight at ambient temperature when the precipitated solid was removed
2. 2
   其他The filtrate was evaporated in vacuo
3. 3
   其他the residue partitioned between ethyl acetate and water
4. 4
   干燥The organic phase was dried (MgSO4)
5. 5
   其他evaporated
6. 6
   其他Purification by flash chromatography on silica
7. 7
   洗涤eluting firstly with 0 to 10% v/v methanol/dichloromethane
8. 8
   其他toluene/ethyl acetate/.880 ammonium hydroxide/ethanol (60:20:10:35 v/v/v/v), gave a cream solid
9. 9
   其他Recrystallisation from iso-propanol

实验过程

iso-Propyl 4-bromoacetylphenoxyacetate (6.3 g) was added to a stirred, cooled (4° C.) solution of 1-(4-pyridyl)piperazine (6.5 g) in acetonitrile (225 ml). Stirring was continued for 1 hour at 4° C., then overnight at ambient temperature when the precipitated solid was removed. The filtrate was evaporated in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was dried (MgSO4) and evaporated. Purification by flash chromatography on silica, eluting firstly with 0 to 10% v/v methanol/dichloromethane and then toluene/ethyl acetate/.880 ammonium hydroxide/ethanol (60:20:10:35 v/v/v/v), gave a cream solid. Recrystallisation from iso-propanol gave the title compound, 2.1 g: m.p. 121°-122° C.; NMR (d6DMSO) δ 8.14 (2H, d), 7.98 (2H, d), 7.02 (2H, d), 6.80 (2H, d), 4.99 (1H, m), 4.85 (2H, s), 3.84 (2H, s), 3.33 (4H, t), 2.62 (4H, t), 1.22 (6H, d); m/e 398 (M+H)+ ; calculated for C22H27N3O4 : C, 66.5; H, 6.9; N, 10.6. found: C, 65.8; H, 6.8; N, 10.4%.

来源