34915-68-9

St resson,Boehringer Ingelheim,Boehringer Ingelheim,1976

Bunitrolol is a beta adrenoceptor antagonist that is used as an antihypertensive and antianginal agent.

ChEBI: Bunitrolol is an aromatic ether.

Epichlorohydrin and 2-cyanophenol are first reacted to give 1-(2- cyanophenoxy)-2,3-epoxypropane.
15 g (0.085 mol) of 1-(2-cyanophenoxy)-2,3-epoxy propane were dissolved in 100 ml of ethanol and 18.6 g (0.255 mol) of t-butylamine were added thereto. After standing for 1 hour at room temperature, the solution was heated at 60°-70°C for 2 hours after which the volatile constituents were distilled off in vacuo. The residue was digested with dilute HCl, and the insoluble constituents were vacuum filtered off. Then the filtrate was made alkaline with NaOH and the precipitating base was taken up in ether. After the ether solution had been dried over MgSO4, the ether was distilled off and the residue was dissolved in ethanol and by addition of ethereal HCl, the hydrochloride was precipitated there from in crystalline form which after recrystallization from ethanol with an addition of ether gave9.8 g of 1-(2- cyanophenoxy)-2-hydroxy-3-t-butylamino propane hydrochloride having a melting point of 163°-165°C.

Antianginal