St resson,Boehringer Ingelheim,Boehringer Ingelheim,1976
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.
