[3-(2-bicyclo[2.2.1]hept-2-ylphenoxy)-2-hydroxypropyl]isopropylammonium chloride

Bornaprolol hydrochloride,Onbio Inc.

1-Isopropylamino-3-[2-(2-norbornylexo)phenoxy]propan-2-ol:
24.5 g (0.13 moles) 2-(2-norbornylexo)phenol (L. A. KHEIFITS and A. E. GOL'DOVSKII, Zh. Obshch. Khim., 1963, 33, 2048), 350 ml anhydrous toluene and 3 g (0.13 mole) metallic sodium are introduced into a three-neck flask through which a stream of nitrogen flows. The reaction mixture is refluxed until the liberation of hydrogen ceases, then the solvent is driven off under reduced pressure and the residue is taken up in 250 ml tetrahydrofuran. 24 g (0.26 mole) epichlorohydrin are then added and the mixture is heated under reflux for 6 hours. An extraction with ether is then undertaken, the organic phase is washed with water, dried and the solvent is evaporated. 25 g 2-(2- norbornylexo)-1-phenoxy-2,3-epoxypropane are thus obtained in the form of an oil.
15 g (0.06 mole) of the preceding product are dissolved in 50 ml isopropylamine. After 4 days contact, the excess amine is evaporated under reduced pressure, then an extraction with ether is carried out. After washing with water and drying, the ethereal phase is saturated with gaseous hydrochloric acid. The precipitate formed is washed abundantly with ether then crystallized from an acetone/ethanol mixture (3/2). 16 g of the desired product in the form of the hydrochloride are thus obtained, having a melting point of 189°-191°C.

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