53684-49-4

Adobiol,Yoshitomi,Japan,1974

Bufetolol is a β-adrenergic blocking agent and it inhibits the activation of adenyl cyclase.

ChEBI: Bufetolol is an aromatic ether.

The preparation of a similar compound in which a methoxyethoxy group replaces the tetrahydrofurfuryloxy group in Bufetrol is described in the following example. Nine grams of o-(2-methoxyethoxy)phenol is suspended in 50 milliliters of water containing 3.7 grams of potassium hydroxide, and 5.5 grams of epichlorhydrin is added thereto with stirring. The mixture is stirred at room temperature for 7 hours, and then extracted with two 50 milliliter portions of benzene. The extract is washed with water, dried over anhydrous magnesium sulfate and the benzene is distilled off to give 8.5 grams of oily 1- (2,3-epoxypropoxy)-2-(2-methoxyethoxy)benzene showing nD 20 = 1.5257. This compound has the methoxyethoxy group in place of the 2- tetrahydrofurfuryloxy group in Bufetrol.
To a solution of 1-(2,3-epoxypropoxy)-2-(2-tetrahydrofurfuryloxy)benzene in methanol are added tert-butylamine and water, the mixture is allowed to stand at 25°-30°C for 72 hours, and then the methanol is distilled off. The residue is dissolved in toluene and the solution is extracted twice with 5% oxalic acid. The aqueous extract is dried over potassium carbonate and concentrated to give Bufetrol.

Antiarrhythmic