Hexamethylenetetramine → 6-Hydroxy-2-(4-isopropyl-piperazin-1-yl)-benzothiazole-7-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4-Isopropyl-piperazin-yl)-benzothiazol-6-ol (76 mg, 0.027 mmol), hexamethylenetetramine (153 mg, 1.10 mmol) and trifluoroacetic acid (2 mL) was stirred in a closed vessel under argon atmosphere at 120° C. for 1 h. The mixture was cooled to room temperature then 10 ml, of water was added. The pH of the mixture was adjusted to 8 by portionwise addition of saturated NaHCO3 solution, and extracted with dichloromethane (3×15 mL). After drying (MgSO4), filtration and evaporation of the solvent, the residue was purified by column chromatography (Kieselgel 60) using chloroform-methanol 49:1 as eluent followed by trituration with diethyl ether and n-hexane. The title compound (14 mg, 0.040 mmol, 14%) was obtained as a yellow solid.

Provenance & Evidence