Reaction #2315

Reaction equation

iso-Propyl 4-bromoacetylphenoxyacetate

1-(4-pyridyl)piperazine

→

title compound

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

Solvents

acetonitrile

Conditions

Workup

1. 1
   Otherovernight at ambient temperature when the precipitated solid was removed
2. 2
   OtherThe filtrate was evaporated in vacuo
3. 3
   Otherthe residue partitioned between ethyl acetate and water
4. 4
   DryingThe organic phase was dried (MgSO4)
5. 5
   Otherevaporated
6. 6
   OtherPurification by flash chromatography on silica
7. 7
   Washeluting firstly with 0 to 10% v/v methanol/dichloromethane
8. 8
   Othertoluene/ethyl acetate/.880 ammonium hydroxide/ethanol (60:20:10:35 v/v/v/v), gave a cream solid
9. 9
   OtherRecrystallisation from iso-propanol

Procedure

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%.

Source