Dimethyl Sulfoxide → HCID 13185701, compound

Participants

Reaction Steps

To a solution of oxalyl chloride (1 mL) in dichloromethane, cooled to −78° C. was added dropwise a solution of dimethyl sulfoxide (1.5 mL) in dichloromethane. The mixture was stirred for 10 minutes and a solution of 6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-ol (Chem. Pharm. Bull. 43, 3, 1995), (1.42 g, 8.7 mmol) in dichloromethane was added to it. After 30 minutes, triethylamine (6 mL) was added to the reaction mixture and it was stirred at ambient temperature for 1 hour and partitioned in dichloromethane/water. The organic layer was dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel, eluting with ethyl acetate to yield the title compound: 1H NMR (300 MHz, CDCl3) δ 8.64 (dd, J=4.58, 1.53 Hz, 1 H), 7.58 (dd, J=7.63, 1.53 Hz, 1 H), 7.33 (dd, J=7.80, 4.75 Hz, 1 H), 2.92 (m, 2 H), 2.80 (m, 2 H), 1.90 (s, 4 H); MS (DCI/NH3) m/z 162 (M+H)+.

Provenance & Evidence