Hydrochloric Acid → HCID 14257566, compound

Participants

Reaction Conditions

Reaction Steps

To 60 ml of a dried dichloromethane solution containing 2.4 ml of oxalyl chloride was added dropwise at -50° C. 12 ml of a dichloromethane solution containing 4.08 ml of dimethylsulfoxide. To the mixture was added dropwise over a period of 20 minutes, while maintaining the temperature at -55° C., 4 ml of a dried dichloromethane solution containing 8.34 g of N-hexyl-N-(2-hydroxypropyl)-5-isoquinolinesulfonamide, followed by stirring at -50° C. to -60° C. for 15 minutes. To the resulting mixture was added 16.8 ml of triethylamine, and the temperature of the mixture was elevated to 15° to 20° C. over a period of 1.5 hours. To the resulting reaction mixture was added 100 ml of water, and the pH was adjusted to 5 with 1N hydrochloric acid solution. The dichloromethane layer was washed with 50 ml of a saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. Then, the dichloromethane was removed under reduced pressure to obtain a residue. The residue thus obtained was subjected to purification by silica gel column chromatography (Wacogel C-200, 200 g; solvent: a 2% methanol solution in chloroform) to obtain 7.17 g of N-acetonyl-N-hexyl-5-isoquinolinesulfonamide.

Provenance & Evidence