反応 #2315

反応方程式

iso-Propyl 4-bromoacetylphenoxyacetate

1-(4-pyridyl)piperazine

→

title compound

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

溶媒

acetonitrile

反応条件

後処理

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

実験手順

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%.

出典