Triethylamine → 1-(2-(4-(2-Bromo-6-methoxy-3,4-dihydronaphthalen-1-yloxy)phenoxy)ethyl)piperidine

Participants

Reaction Conditions

Reaction Steps

To a flask, add 6-methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)-3,4-dihydronaphthalene-2-carboxylic acid (0.4 g, 0.68 mmol), dichloromethane (10 mL), and triethylamine (0.2 mL, 1.43 mmol). Stir the mixture at 25° C. for 10 min. Add N-Bromosuccinimide (0.5 g; 4.13 equiv; 2.81 mmol) in portions. Cool the reaction mixture to room temperature and quench with ice-water. Extract the mixture with ethyl acetate three times and discard the aqueous phase. Dry the combined organic layers over MgSO4, filter, and concentrate to dryness to give 1-(2-(4-(2-Bromo-6-methoxy-3,4-dihydronaphthalen-1-yloxy)phenoxy)ethyl)piperidine as a yellow oil (300 mg).

Provenance & Evidence