Synephrine → N-[(4-chlorophenyl)methyl]-6-[[[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-methyl-amino]methyl]-1-methyl-4-oxo-quinoline-3-carboxamide

Participants

Reaction Steps

A solution of N-(4-chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.09 gm) from Preparation No. 35 in dry DMF (2 mL) containing diisopropylethylamine (0.07 mL) is treated with synephrine (0.05 gm). The reaction mixture is stirred overnight. The reaction mixture is diluted with dichloromethane (50 mL) and washed with water (2×10 mL), brine (10 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue is purified by flash column chromatography eluting with 3% to 6% methanol in dichloromethane and then by recrystallization from toluene to afford 0.09 gm of the title compound as a tan solid.

Provenance & Evidence