반응 #2315

반응 방정식

iso-Propyl 4-bromoacetylphenoxyacetate

1-(4-pyridyl)piperazine

→

title compound

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

용매

acetonitrile

반응 조건

후처리

1. 1
   기타overnight at ambient temperature when the precipitated solid was removed
2. 2
   기타The filtrate was evaporated in vacuo
3. 3
   기타the residue partitioned between ethyl acetate and water
4. 4
   건조The organic phase was dried (MgSO4)
5. 5
   기타evaporated
6. 6
   기타Purification by flash chromatography on silica
7. 7
   세척eluting firstly with 0 to 10% v/v methanol/dichloromethane
8. 8
   기타toluene/ethyl acetate/.880 ammonium hydroxide/ethanol (60:20:10:35 v/v/v/v), gave a cream solid
9. 9
   기타Recrystallisation from iso-propanol

실험 절차

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%.

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