Triethylamine → HCID 69506750, compound

Participants

Reaction Steps

A solution of 4-chloro-3-nitroquinoline (10.96 g, 52.5 mmol) in dichloromethane (200 mL) was cooled to approximately 0° C., and triethylamine (22.0 mL, 158 mmol) and a solution of ethyl 1-(aminomethyl)cyclohexanecarboxylate hydrochloride (11.65 g, 52.5 mmol) in dichloromethane (30 mL) were sequentially added. The reaction was stirred for four hours, and the solvent was removed under reduced pressure. The residue was stirred in deionized water (50 mL) for one hour, and the mixture was extracted several times with dichloromethane. The combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting orange oil was purified by chromatography on silica gel (eluting with 3-5% methanol in dichloromethane) to provide 11.72 g of ethyl 1-{[(3-nitroquinolin-4-yl)amino]methyl}cyclohexanecarboxylate as art orange oil that solidified upon standing.

Provenance & Evidence