Water → N-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-4-oxo-1-[2-(1-piperidyl)ethyl]quinoline-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Preparation No. 5 (0.367 g) is dissolved in DMF (10 mL), and K2CO3 (0.55 g, 4.0 mmol) and 1-(2-chloroethyl)piperidine hydrochloride (0.375 g, 2.0 mmol) are added. The reaction mixture is heated to 90° C. for 3 h, and then allowed to stir at room temperature for 48 h. Water is added and a precipitate formed. The precipitate is filtered and allowed to dry at room temperature and then under reduced pressure to give 0.171 g of a solid. The solid is dissolved in CHCl3 and filtered. The filtrate is concentrated in vacuo and crystallized from ethyl acetate to give 0.066 g of the title compound as a solid.

Provenance & Evidence