Reaktion #1155142

Reaktionsgleichung

N-(4-chlorobenzyl)-1,4-dihydro-6-[3-hydroxy-1-propenyl]-4-oxo-3-quinolinecarboxamide

potassium carbonate

N-(2-chloroethyl)morpholine hydrochloride

→

title compound

N-(4-Chlorobenzyl)-6-(3-hydroxy-1-propenyl)-1-[2-(4-morpholinyl)ethyl]-4-oxo-1,4-dihydro 3-quinolinecarboxamide

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepartitioned between water and chloroform
2. 2
   EinengenThe organic layer is concentrated in vacuo
3. 3
   Sonstigeto give a brown oil
4. 4
   WaschenColumn chromatography (elution with 1-7% MeOH/CHCl3)
5. 5
   Sonstigefollowed by crystallization from EtOAc/hexane

Vorschrift

A mixture of N-(4-chlorobenzyl)-1,4-dihydro-6-[3-hydroxy-1-propenyl]-4-oxo-3-quinolinecarboxamide from Preparations No. 11 and 12 (0.52 g) is dissolved in DMF (4 mL), and potassium carbonate (0.78 g) and N-(2-chloroethyl)morpholine hydrochloride (0.52 g) are added. The mixture is heated at 90° C. for 2 h and then partitioned between water and chloroform. The organic layer is concentrated in vacuo to give a brown oil. Column chromatography (elution with 1-7% MeOH/CHCl3) followed by crystallization from EtOAc/hexane gave the title compound as a mixture of isomers. The mixture is then purified by HPLC chromatography on a 0.46×25 cm Chiralcel OD-H column eluting with EtOH at a rate of 0.5 mL/min. This gave 0.161 g of the alkene mixture as approximately a 2:1 mixture of the trans:cis isomers, which is crystallized from ethyl acetate to give 0.13 g of the title compound as a hydrate.

Quelle