Epanolol

[1] developed by Imperial Chemical Industries.

[2] The ester methyl 4-benzyloxyphenylacetate (1) is treated with ethylenediamine to give the amide (3).

Separately, 2-cyanophenol (4) is reacted with epichlorohydrin and sodium hydroxide to produce the benzonitrile derivative (5).

Combination of (3) and (5) by heating in propanol gives (6).

Lastly, catalytic hydrogenation removes the benzyl protecting group and yields epanolol.