Réaction #2296

Équation de réaction

methyl 4-bromoacetylphenoxyacetate

1-(4-pyridyl)piperazine

→

title compound

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

Solvants

acetonitrile

acetonitrile

Conditions de réaction

Traitement

1. 1
   Filtrationthe solution was filtered
2. 2
   Autrethe filtrate evaporated in vacuo
3. 3
   AutreThe solid residue was triturated with water (50 ml)
4. 4
   Autredried
5. 5
   FiltrationThe suspension was then filtered
6. 6
   Concentrationthe filtrate concentrated to a small volume
7. 7
   AutrePurification by flash chromatography on neutral alumina eluting first with dichloromethane

Mode opératoire

A solution of methyl 4-bromoacetylphenoxyacetate (4.3 g) in acetonitrile (50 ml) was added dropwise over 40 minutes to a stirred solution of 1-(4-pyridyl)piperazine (4.9 g) in acetonitrile (100 ml). Stirring was continued for a further 1.5 hours, then the solution was filtered and the filtrate evaporated in vacuo. The solid residue was triturated with water (50 ml), then dried and suspended in methylene chloride (50 ml). The suspension was then filtered and the filtrate concentrated to a small volume. Purification by flash chromatography on neutral alumina eluting first with dichloromethane, then 0.5% v/v methanol/dichloromethane and finally 1% v/v methanol/dichloromethane gave the title compound, 1.93 g, as a solid: m.p. 150°-152° C.; NMR(d6DMSO) δ 8.14(2H,d), 7.98(2H,d), 7.03(2H,d), 6.78(2H,d), 4.90(2H,s), 3.83(2H,s), 3.72(3H,s), 3.34(4H,bt), 2.65(4H,bt); m/e 370 (M+H)+ ; calculated for C20H23N3O4 : C, 65.0; H, 6.3; N, 11.4 found: C 65.2; H, 6.4; N,

Source