Reaktion #2296

Reaktionsgleichung

methyl 4-bromoacetylphenoxyacetate

1-(4-pyridyl)piperazine

→

title compound

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

Lösungsmittel

acetonitrile

acetonitrile

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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,

Quelle