Hydrogen Bromide → HCID 66732651, compound

Participants

Reaction Steps

Trans-methyl 2-(3,5-dichlorophenyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (300 mg, 0.81 mmol) was diluted with hydrogen bromide (33% in AcOH, 4.3 mL, 24.24 mmol) and stirred at ambient temperature for 48 h. Evaporated and the residue purified by preparative HPLC (Instrument: FractionLynx II, Mobilphase: gradient 5-95% MeCN in 0.2% NH3, pH 10, Column: Xbridge Prep C18 5 μm OBD 19*150 mm) to yield 5-(trans-2-(3,5-dichlorophenyl)piperidin-4-yl)isoxazol-3(2H)-one (162 mg, 64%). 1H NMR (600 MHz, CDCl3) δ 1.77-2.17 (m, 4H), 2.66-2.74 (m, 1H), 2.82-2.89 (m, 1H), 3.12-3.18 (m, 1H), 3.79 (d, 1H), 6.06 (s, 1H), 7.44-7.51 (m, 3H). HRMS Calculated for [C14H14Cl2N2O2+H]+: 313.0511. Found: 313.0513

Provenance & Evidence