1,4-Dioxane hydrochloride → Methyl 5-chloro-2-methyl-3-(piperidin-4-yloxy)benzoate, hydrochloride

Participants

Reaction Steps

A solution of tert-butyl 4-(5-chloro-3-(methoxycarbonyl)-2-methylphenoxy)piperidine-1-carboxylate (300 mg, 0.782 mmol) in DCM (3 mL) was treated with 4 M HCl/dioxane (3908 μl, 15.63 mmol) and stirred for 1 h at RT. The slurry was filtered and dried to give methyl 5-chloro-2-methyl-3-(piperidin-4-yloxy)benzoate, hydrochloride (0.185 g, 0.578 mmol, 74% yield). 1H NMR (400 MHz, DMSO-d6) δ 1.76-1.94 (m, 2 H) 2.02-2.16 (m, 2 H) 2.30 (s, 3 H) 2.99-3.13 (m, 2 H) 3.16-3.26 (m, 2 H) 3.83 (s, 3 H) 4.78 (dt, J=6.95, 3.60 Hz, 1 H) 7.34 (d, J=2.02 Hz, 1 H) 7.40 (d, J=2.02 Hz, 1 H) 8.83 (br. s., 2 H). MS(ES) [M+H]+ 284.1.

Provenance & Evidence