Diethylethanolamine → Diethyl[2-(4-nitrophenoxy)ethyl]amine

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (4.8 g, 50% in oil, 100 mmol) was added to a solution of 2-diethylamino-ethanol (11.7 g, 100 mmol) (Aldrich) in tetrahydrofuran (500 mL) and stirred for 15 minutes and then heated to 40° C. for an additional 15 minutes. The mixture was cooled to −10° C. and a solution of 1-fluoro-4-nitrobenzene (10 g, 70 mmol) in tetrahydrofuran (50 mL) was added dropwise and stirred at room temperature for 2 hours. The solvent was evaporated and the residue was dissolved in dichloromethane and washed twice with a 4:1 water/brine mixture. The dichloromethane was evaporated under vacuo and the residue chromatographed on silica gel using 1:1 hexane/ethyl acetate, ethyl acetate, then 20% methanol in dichloromethane. The product fractions were concentrated in vacuo, dissolved in ether, treated with activated charcoal, filtered through Celite™ and concentrated to give 9 g, (54%) of diethyl-[2-(4-nitro-phenoxy)-ethyl]-amine.

Provenance & Evidence