Hydrochloric Acid → 2-(1-Methoxy-naphthalen-2-yl)-1-methylethylamine hydrochloride

Participants

Reaction Conditions

Reaction Steps

The product from Step C (3.04 g, 18.3 mmol) was dissolved in ethanol (50 mL), ammonium acetate (1.55 g, 20.10 mmol) was added followed by nitroethane (2.75 g, 36.5 mmol). The reaction mixture was stirred at 70° C. for 3 h and then the solvent was removed. The residue was dissolved in ethyl acetate (100 mL) and washed with water (2×100 mL). The organic layer was dried (MgSO4) and concentrated to give a solid, which was dissolved in anhydrous tetrahydrofuran (100 mL) and cooled to 0° C. To this solution, a 1 M solution of lithium aluminum hydride in tetrahydrofuran (73 mL) was added and the reaction mixture allowed to warm to room temperature and stirred for 2 h followed by heating at reflux for an additional 2 h. Excess lithium aluminum hydride was consumed by adding ethyl acetate (50 mL) and then water (400 mL). The organic material was extracted with dichloromethane, dried (MgSO4), and concentrated to give an oil which was transformed to hydrochloride salt by adding 1 M solution of hydrogen chloride in diethyl ether. The white solid was collected by filtration: 1H NMR (DMSO-d) δ 1.14 (d, 3H, CH3), 2.94 (m, 2H, CH2), 3.52 (m, 1H, CH), 3.89 (s, 3H, OCH3), 7.38–8.06 (m, 6H, Ar—H), 8.19 (bs, NH3+); MS 216 (M+1). Analysis. Calcd. for C14H17NO.HCl.0.3 H2O: C, 65.39; H, 7.21; N, 5.56. Found: C, 65.16; H, 7.07; N, 5.42.

Provenance & Evidence