Reaktion #2315

Reaktionsgleichung

iso-Propyl 4-bromoacetylphenoxyacetate

1-(4-pyridyl)piperazine

→

title compound

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

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeovernight at ambient temperature when the precipitated solid was removed
2. 2
   SonstigeThe filtrate was evaporated in vacuo
3. 3
   Sonstigethe residue partitioned between ethyl acetate and water
4. 4
   TrocknenThe organic phase was dried (MgSO4)
5. 5
   Sonstigeevaporated
6. 6
   SonstigePurification by flash chromatography on silica
7. 7
   Wascheneluting firstly with 0 to 10% v/v methanol/dichloromethane
8. 8
   Sonstigetoluene/ethyl acetate/.880 ammonium hydroxide/ethanol (60:20:10:35 v/v/v/v), gave a cream solid
9. 9
   SonstigeRecrystallisation from iso-propanol

Vorschrift

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%.

Quelle