Propanal → 2-methyl-4-[4-[(E)-pent-1-enyl]sulfonylpiperazin-1-yl]quinoline

Participants

Reaction Conditions

Reaction Steps

4-[4-(Diethoxyphosphorylmethylsulfonyl)piperazin-1-yl]-2-methyl-quinoline (47 mg, 0.106 mmol) was dissolved in anhydrous THF (1 ml), lithium bromide (11.1 mg, 0.128 mmol) and propionaldehyde (9.2 μl, 0.128 mmol) were added with stirring and the mixture was cooled to −10° C. DBU (15.2 μl, 0.102 mmol) was added, and the temperature was raised to room temperature. Stirring was continued for 30 minutes, the reaction mixture was diluted with dichloromethane, washed with 5% sodium bicarbonate solution (2×), water and evaporated to dryness. The residue was purified with preparative HPLC (gradient of water containing 0.1% ammonia and acetonitrile). 5 mg of a solid were obtained (0.014 mmol, 14%).

Provenance & Evidence