O-Methyltyramine → 2-[(4-Methoxyphenethyl)aminomethyl]-1,2,3,4-tetrahydronaphthalene

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Reaction Steps

A solution of 2-bromomethyl-1,2,3,4-tetrahydronaphthalene (1.33 g, 5.91 mmol), 4-methoxyphenethylamine (1.79 g, 11.8 mmol) in 50 ml of EtOH was refluxed for 48 hrs. After removal of EtOH in vacuo, the residue was dissolved in 100 ml of CHCl3, washed with 10% K2CO3, H2O, sat'd brine then dried over Na2SO4. Filtration followed by evaporation of solvent gave a yellow oil, which was purified by chromatography (SiO2, MeOH: CHCl3, 5:95) to give the final product as a yellowish oil (1.03 g, 58.9%). The product was converted to HCl salt, crystallization with MeOH/Et2O gave a white powder; mp 274°-275° C.; Calcd. for C20H25NO·HCl: C 72.37, H 7.91, N 4.22: Found: C 72.40, H 7.76, N 4.13.

Provenance & Evidence