Aluminium lithium hydride → 2-[Phenethylaminomethyl]-1,2,3,4-tetrahydronaphthalene

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Reaction Steps

The solution of N-(2-phenylethyl) 1,2,3,4-tetrahydro-2-naphthoic amide (693 mg, 2.48 mmol) in 15 ml of THF was treated with LiAlH4 (149 mg, 3.72 mmol). The mixture was refluxed for 4 hrs then carefully quenched by addition of solid Na2SO4 ·10H2O. After stirred at r.t. overnight, the solid was removed by filtration and concentration of filtrate in vacuo gave a colorless oil (604 mg, 91.7%). The product was converted to HCl salt, crystallization with MeOH/Et2O gave a white powder; mp 260°-263° C.; Calcd for C19H23N·HCl: C 75.58, H 8.03, N 4.64: Found: C 75.77, H, 8.24, N 4.45.

Provenance & Evidence