Benzyl acetone → 5-[1-Hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl]-o-anisamide

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Reaction Steps

To a solution of the above 5-(2-amino-1-hydroxyethyl)-o-anisamide in ethanol (70ml) was added benzyl acetone (1.5g), and the mixture was gently refluxed for 1 hour. The cooled solution was then added to a suspension of pre-reduced 5% platinum on charcoal (0.4g) in ethanol (10 ml) and hydrogenated until uptake was complete. Hydrogen uptake was complete within 14 hours. The catalyst and solvent were removed to leave 5-[1-hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl]-o-anisamide as an oil (2.36g) which slowly crystallised on rubbing with ether, m.p. 110°-148°.

Provenance & Evidence