Cyclopropylamine → HCID 178527305, compound

Participants

Reaction Conditions

Reaction Steps

A solution of toluene-4-sulfonic acid 2-(3-benzenesulfonyl-1H-indazol-5-yloxy)-ethyl ester (0.336 g, 0.711 mmol) and cyclopropylamine (1.0 mL, 14 mmol) in THF (8 mL) was stirred at 70° C. for 6 hours in a sealed tube. Additional cyclopropylamine (1.0 mL, 14 mmol) was added, and the reaction mixture was stirred for 6 hours at 80° C. in a sealed tube. After cooling somewhat, the reaction mixture was solvent evaporated and partitioned in ethyl acetate and aqueous sodium bicarbonate. The organic phase was then washed with water and brine, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography using 5% methanol in chloroform. After drying in vacuo at 55° C. temperature for 25 minutes, [2-(3-benzenesulfonyl-1H-indazol-5-yloxy)-ethyl]-cyclopropyl-amine as a light yellow foam (0.127 g, 50.0%) was obtained. This was dissolved in chloroform, and ethereal hydrochloride was added. The mixture was concentrated and dried in vacuo at 75° C. for 16.5 hours to yield the hydrochloride as a buff solid (0.131 g): MP: 184-5° C. dec.; Mass Spectrum (+EI, [M+H]+) m/z 358.

Provenance & Evidence