Hydrochloric Acid → 1-(2-(4-(2-(5-Fluorothiophen-2-yl)-6-methoxynaphthalen-1-yloxy)phenoxy)ethyl)piperidine

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Reaction Conditions

Reaction Steps

Add 1-(2-(4-(6-methoxy-2-(thiophen-2-yl)naphthalen-1-yloxy)phenoxy)ethyl)piperidine (153 mg, 0.4 mmol) and tetrahydrofuran (3.3 mL) to a screw-cap vial under argon. Cool the resulting solution to −78° C. Add n-butyl lithium (1.6M in hexanes; 230 μL, 0.4 mmol) dropwise. Warm the resulting solution to 0° C. and stir for 30 min. Add a solution of N-fluorobenzenesulfonimide (210.0 mg; 0.6 mmol) in tetrahydrofuran (500 μL). Allow the resulting mixture to warm to room temperature and stir for 2 hours. Add 1M HCl, dilute with ether and pass through an SCX acidic ion exchange column. Flush the column with methanol then elute desired material with 2M ammonia in methanol. Concentrate the ammonia containing eluent to give a yellow solid. Purify the yellow solid on a silica gel flash chromatography to obtain the title compound (59.0 mg, 0.1 mmol): mass spectrum (m/z): 478 (M+1).

Provenance & Evidence