Morpholine → 4-(4-Nitrobenzyl)morpholine

Participants

Reaction Steps

4-Nitrobenzyl bromide is treated with morpholine and potassium carbonate in acetone to give 4-(4-Nitrobenzyl)morpholine (G-1). The nitro group is reduced with platinum and hydrogen gas to afford the aniline (G-2) which is then treated with [(1-ethoxycyclopropyl)-oxy]trimethylsilane and sodium cyanoborohydride to give the N-cyclopropyl aniline (G-3). Reaction with diethyl ethoxymethylenemalonate in pyridine affords the enamine (G-4) which is cyclized with polyphosphoric acid to the quinoline (G-5). Treatment with p-chlorobenzylamine at elevated temperature converts the ester to the amide (G-6).

Provenance & Evidence