Diethylamine → N-ethyl-N-[(4-nitrophenyl)methyl]ethanamine

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Reaction Steps

P-nitrobenzyl bromide (5.0 g) was added to a methanol solution (50 mL) of diethylamine (16.9 g), and stirred at room temperature for 3 hours. Methanol was evaporated off from the reaction liquid under reduced pressure, and water was added to the resulting residue, and extracted with ethyl acetate. The organic layer was extracted with 1 N hydrochloric acid, and the aqueous layer was neutralized with aqueous ammonium solution. The aqueous layer was extracted with ethyl acetate, and the organic layer was dried with anhydrous magnesium sulfate, and then the solvent was evaporated off under reduced pressure to obtain N,N-diethyl-N-(4-nitrobenzyl)amine (4.8 g) as an orange oily substance.

Provenance & Evidence