Réaction #2328

Équation de réaction

Methyl 4-(2,2-dimethylbromoacetyl)phenoxyacetate

1-(4-pyridyl)piperazine

→

title compound

Methyl 4-[2-[4-(4-pyridyl)piperazin-1-yl]-2,2-dimethyl-acetyl]phenoxyacetate

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Autrethe solid formed
2. 2
   Autrewas removed by filtration
3. 3
   Autrethe filtrate evaporated
4. 4
   Autreto give an oil
5. 5
   AutrePurification by flash chromatography on silica
6. 6
   Lavageeluting with 0.5 to 4.0% v/v methanol/dichloromethane

Mode opératoire

Methyl 4-(2,2-dimethylbromoacetyl)phenoxyacetate (1.58 g) was added to a stirred solution of 1-(4-pyridyl)piperazine (1.63 g) in acetonitrile (40 ml). After 34 days, the solid formed was removed by filtration and the filtrate evaporated to give an oil. Purification by flash chromatography on silica, eluting with 0.5 to 4.0% v/v methanol/dichloromethane gave the title compound, 240 mg, as a white foam: NMR (d6DMSO) δ 8.49 (2H, d), 8.12 (2H, d), 6.96 (2H, d), 6.77 (2H, d), 4.87 (2H, s), 3.69 (3H, s), 3.28 (4H, t), 2.58 (4H, t), 1.25 (6H, s); m/e 398 (M+H)+ ; calculated for C22H27N3O4.0.25H2O: C, 65.7; H, 6.8; N, 10.4. found: C, 65.3; H, 6.9; N, 10.4%.

Source