Chlorosuccinimide → HCID 18950547, compound

Participants

Reaction Steps

A solution of 387 mg of 1-(8-methyl-1,2,4-triazolo-[4,3-b]pyridazin-6-yl)-3-(phenylselenyl)-4-piperidinol in dichloromethane at room temperature was treated with a solution of 147 mg of N-chlorosuccinimide in 3 ml of dichloromethane and stirred at room temperature. A white precipitate formed. After 15 minutes, 305 mg of 1,8-diazabicyclo [5,4,0]undec-7-ene was added and stirring continued at room temperature for 20 hours. This resulted in a very dark-colored solution. The reaction volume was reduced at the rotary evaporator and the solution put directly on a silica gel (20 g) flash chromatography column. After rinsing the material on the column with dichloromethane, it was eluted with 95% dichloromethane/5% ethanol (10% concentrated ammonium hydroxide). The clean fractions were combined to give, on evaporation of the solvent, a tan viscous oil which slowly crystallized to give 1-(8-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)-1,4,5,6-tetrahydro-4-pyridinol melting at about 171°-173° C.

Provenance & Evidence