Diethylethanolamine → HCID 59497147, compound

Participants

Reaction Steps

To a suspension of sodium hydride (60% in mineral oil, 5.25 g, 131.1 mmol) in anhydrous THF (90 mL) a solution of N,N-diethyl-2-hydroxyethylamine (15.30 g, 131.1 mmol) in anhydrous THF (60 mL) was slowly added. The mixture was stirred at room temperature for 20 minutes and a solution of 4-chloro-2-methyl-[1,10]phenanthroline(6.00 g, 26.2 mmol) in anhydrous THF (90 mL) was slowly added. The reaction mixture was refluxed for 18 hours and then allowed to cool down to room temperature, quenched with 1N HCl and evaporated. The residue was redissolved in 1N NaOH (150 mL) and extracted with methylene choride (3×200 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was washed with hexane and purified by flash chromatography (SiO2, MeOH/DCM, 1:40) to yield the pure product as an orange oil (5.1 g, 63%).

Provenance & Evidence