Hydrochloric Acid → 4-({[2'-Fluoro-4'-(methylsulfonyl)-4-biphenylyl]oxy}methyl)piperidine hydrochloride

Participants

Reaction Steps

1,1-Dimethylethyl 4-({[2′-fluoro-4′-(methylsulfonyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylate (Example 65, 0.484 g, 1.04 mmol) was dissolved in 1,4-dioxane (20 mL). To this solution was added ether (15 mL), followed by addition of 4.0M HCl in 1,4-dioxane (15 mL) and 2M HCl in ether (15 mL). The reaction mixture was stirred at ambient temperature overnight. The white solid was collected via filtration and washed with ether to yield 0.386 mg (92%) of 4-({[2′-fluoro-4′-(methylsulfonyl)-4-biphenylyl]oxy}methyl)piperidine hydrochloride as a white solid. 1H NMR (400 MHz, CD3OD): δ 7.85-7.50 (m, 3H), 7.56 (d, 2H, J=7.3 Hz), 7.06 (d, 2H, J=8.7 Hz), 3.98 (d, 2H, J=5.9 Hz), 3.50-3.40 (m, 2H), 3.17 (s, 3H), 3.10-3.00 (m, 2H), 2.25-2.05 (m, 3H), 1.70-1.55 (m, 2H); LRMS (ESI), m/z 364 (M+H).

Provenance & Evidence