Hydrochloric Acid → 2-[4-(Methylsulfonyl)phenyl]-5-[(4-piperidinylmethyl)oxy]pyridine dihydrochloride

Participants

Reaction Steps

A solution of 1,1-dimethylethyl 4-[({6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate (5.47 g, 12.25 mmol) in 1,4-dioxane (70 mL) was treated with 4.0M HCl in 1,4-dioxane (30 mL, 122 mmol). The reaction mixture was stirred at ambient temperature for 16 h. Diethyl ether was added to the reaction mixture and the resulting solid was collected by filtration. The crude product was then dissolved in methanol and filtered. The filtrate was concentrated to give 4.36 g (85%) of 2-[4-(methylsulfonyl)phenyl]-5-[(4-piperidinylmethyl)oxy]pyridine dihydrochloride as a white solid. 1H NMR (400 MHz, CD3OD): δ 8.62 (d, 1H, J=2.7 Hz), 8.31 (d, 1H, J=2.7 Hz), 8.23-8.12 (m, 5H), 4.22 (d, 2H, J=6.1 Hz), 3.51-3.46 (m, 2H), 3.20 (s, 3H), 3.13-3.05 (m, 2H), 2.34-2.23 (m, 1H), 2.16-2.10 (m, 2H), 1.75-1.64 (m, 2H); LRMS (APCI), m/z 347 (M+H).

Provenance & Evidence