Reaktion #2331

Reaktionsgleichung

1-(4-Pyridyl)piperazine

methyl 4-(4-bromomethylphenyl)butyrate

→

title compound

Methyl 4-[4-[4-(4-pyridyl)piperazin-1-yl]methylphenyl]-butyrate

Lösungsmittel

acetonitrile

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter 30 minutes the resulting precipitate was removed by filtration
2. 2
   Einengenthe filtrate concentrated in vacuo
3. 3
   Sonstigeto give a yellow oil
4. 4
   SonstigePurification by flash chromatography on silica
5. 5
   Wascheneluting with 0 to 4% v/v methanol/dichloromethane
6. 6
   Sonstigegave a solid
7. 7
   SonstigeTrituration with ether and removal of the insoluble solid
8. 8
   Sonstigegave a clear solution

Vorschrift

1-(4-Pyridyl)piperazine (1.63 g) was dissolved in warm acetonitrile (25 ml), the solution cooled to 30° C. and with stirring, a solution of methyl 4-(4-bromomethylphenyl)butyrate in acetonitrile (5 ml) added. After 30 minutes the resulting precipitate was removed by filtration and the filtrate concentrated in vacuo to give a yellow oil. Purification by flash chromatography on silica, eluting with 0 to 4% v/v methanol/dichloromethane gave a solid. Trituration with ether and removal of the insoluble solid gave a clear solution. Concentration of this solution gave the title compound, 0.90 g, as a white fluffy solid: m.p. 126°-127° C.; NMR (d6DMSO) δ 8.14 (2H, d), 7.24 (2H, d), 7.14 (2H, d), 6.77 (2H, d), 3.59 (3H, s), 3.48 (2H, s), 3.30 (4H, t), 2.59 (2H, t), 2.47 (4H, t), 2.32 (2H, t), 1.63 (2H, m); m/e 354 (M+H)+ ; calculated for C21H27N3O2.0.25H2O: C, 70.4; H, 7.7; N, 11.7. found: C, 70.6; H, 7.6; N, 11.7%.

Quelle