Bis(2-Methoxyethyl)amine → 1,2,3,4-Tetrahydro-8-methoxy-N,N-bis(2-methoxyethyl)-2-naphthalenamine

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Reaction Steps

A solution of 1.76 g (10 mmol) 8-methoxy tetralone, 2.66 g (20 mmol) N,N-bis(-2methoxyethyl)amine, and 25 mg p-toluenesulfonic acid in toluene was heated to reflux under a N2 atmosphere. The flask was equipped with a Dean-Stark trap to collect H2O. TLC analysis was used to monitor the reaction. After 48 hours, the solvent was removed in vacuo. The crude ene-amine was hydrogenated using 450 mg 10% pd/C in 50 mL MeOH at 50 psi H2 for 24 hours. The reaction mixture was filtered over celite and the filtrate purified by liquid chromatography on 400 g of silica gel-60 (230-400 mesh), eluting with hexane/ethyl acetate/isopropanol (10:5:1). Fractions homogeneous by TLC were combined and concentrated in vacuo to give pure title compound as a yellow oil (2.3 g, 80%).

Provenance & Evidence