Aluminum(III) Chloride → N1,N1-Diethyl-1-(naphthalen-1-yl)-1,2-ethanediamine

Participants

Reaction Steps

To a suspension of 0.76 g (0.02 mol) of lithium aluminum hydride in 100 mL of dry diethyl ether under a nitrogen atmosphere and cooled to -10° to 0° C. add carefully in portions 10.67 g (0.08 mol) of aluminum chloride. When the initial reaction has ceased add dropwise a solution of 2.68 g (0.01 mol) of α-azidomethyl-N,N-diethyl-1-naphthalenemethanamine in 50 mL of diethylether. When the addition is complete allow the reaction mixture to warm to room temperature. Follow the progress of the reaction by thin-layer chromatography on silica gel. At the completion of the reaction carefully quench the excess reducing agent by the addition of sodium sulfate decahydrate. Filter the solids and wash the solids with 500 mL of hot methylene chloride. Dry the filtrate over anhydrous sodium sulfate. Filter the drying agent and remove the solvent in vacuo to obtain the title compound.

Provenance & Evidence