A solution of 32.8 g (0.2 m) of methyl 2-(4-hydroxyphenyl)ethyl ketone and
42.6 g (0.2 m) of 1-(4-hydroxyphenyl)-2-aminoethanol in 380 ml of ethanol containing 3.8 g of 5% palladium on carbon was stirred for 16 h at 60°C
under hydrogen at 55 psi. The reaction mixture was then filtered, and the
filtrate was diluted by addition of 350 ml of water. The aqueous mixture was
concentrated to a volume of about 400 ml, and then washed with
dichloromethane.
The aqueous mixture was acidified by addition of 50 ml of conc. hydrochloric
acid. After standing at room temperature for 2 h, the aqueous acid mixture
was filtered and the filter cake was washed with 40 ml of ice water and dried
at 50°C in vacuum to provide 47.0 g of 1-(4-hydroxyphenyl-2-
propylamino]ethanol hydrochloride, melting point 124-129°C.
The 1-(4-hydroxyphenyl)-2-[1-methyl-3-(4-hydroxyphenyl)propylamino]
ethanol was obtained by treatment of 1-(4-hydroxyphenyl-2-
propylamino]ethanol hydrochloride with sodium hydroxide.
