Bromine → HCID 22041764, compound

Participants

Reaction Steps

To a cold heterogeneous solution (ice bath) of 2-(4-methoxy-naphthalen-2-yl) 1-methyl-ethylamine hydrochloride (0.10 g, 0.39 mmol, Example 11) in dichloromethane, was added bromine (0.07 g, 0.43 mmol) via syringe. After 1 h the volatiles were evaporated and the residue was partitioned in a mixture of ethyl acetate (20 mL) and a saturated aqueous solution of bicarbonate (20 mL). The organic layer was separated, dried (MgSO4), and concentrated in vacuo. The residue was dissolved in ethyl ether (20 mL) and the free amine was transformed to its correspondent hydrochloride salt by adding 1 M solution of hydrogen chloride in ethyl ether. The solid formed was collected by filtration (80 mg): 1H NMR (DMSO-d6) δ 1.21 (d, 3H, CH3), 3.24 (m, 2H), 3.60 (m, 11H), 3.66 (m, 1H), 4.02 (s, 3H, OCH3), 7.03 (s, 1H, Ar—H), 7.48–7.75 (m, 2H, Ar—H), 7.96 (m, 3H, NH3+), 8.17 (m, 2H, Ar—H); MS 296 (M+1).

Provenance & Evidence