Zoniclezole Usage And Synthesis

Originator

Zoniclezole hydrochloride,GASTHAUS

Uses

Anticonvulsant.

Manufacturing Process

A solution of n-butyl lithium in hexane (2.1 M, 9.2 ml, 0.019 mole) is added dropwise to a solution of diisopropylamine (0.021 mole) in anhydrous tetrahydrofuran (40 ml) at -40°C (dry ice/isopropanol bath). After standing at this temperature for 10 minutes, the cold solution is added dropwise to a stirred, cooled (-60°C) solution of 5-chloro-3-[(1H-imidazol-1-yl)ethyl]-1,2-benzisoxazole (0.019 mole) in anhydrous tetrahydrofuran (40 ml). The resulting deep red colored reaction mixture is stirred at -60°C for 30 minutes and then iodomethane (4.1 g, 0.029 mole) is added all at once. The reaction is stirred at -60°C for 1 hour and then without external cooling for a further 2 hours. Water (100 ml) and ethyl acetate (100 ml) are then added and the organic solution is separated and extracted with 3 N hydrochloric acid (2x30 ml). The combined acid extracts are subsequently made basic (pH 8) with 2 N sodium hydroxide and the product is extracted into ethyl acetate (2x50 ml). The combined extracts are dried over anhydrous sodium sulfate, filtered and evaporated in vacuum to afford an oil which solidifies on standing. The crude 5-chloro-3-[1-(1H-imidazol-1-yl)ethyl]-1,2-benzisoxazole, is recrystallised from isopropanol, When a warm solution of this material in isopropanol is treated with a small excess of ethereal hydrogen chloride, the hydrochloride salt 5-chloro-3-[1-(1H-imidazol-1-yl)ethyl]-1,2-benzisoxazole hydrochloride is obtained, MP: 168-170°C.

Therapeutic Function

Anticonvulsant

Zoniclezole(121929-20-2)Related Product Information

• C-ISOXAZOL-3-YL-METHYLAMINE
• 5-CHLORO-1,2-BENZISOXAZOLE
• 3-METHYL-1,2-BENZISOXAZOLE
• 1,2-BENZISOXAZOLE, 5-CHLORO-3-METHYL-
• 1,2-BENZISOXAZOLE
• Zoniclezole