Hydrochloric Acid → HCID 14210576, compound

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Reaction Steps

4-Amino-3,5-dichloro-α-[[[6-[4-(3-hydroxy-2-pyridinyl)butoxy]hexyl](phenylmethyl)amino]methyl]benzenemethanol (0.49 g) was hydrogenated over pre-reduced 10% palladium oxide on carbon (50% aqueous paste, 100 mg) in ethanol (10 ml) containing hydrochloric acid (conc. HCl/ethanol, 1:9 v/v, 1.6 ml). The catalyst was removed by filtration through hyflo, the solvent was evaporated and the residual oil was partitioned between 8% sodium bicarbonate (15 ml) and ethyl acetate (15 ml). The organic layer was washed with 8% sodium bicarbonate (10 ml), water (10 ml) and brine (10 ml), dried and concentrated to a yellow oil which was purified by FCC eluting with System C (95:5:1) to give a pale yellow oil which was triturated with ether to give the title compound as a white solid (215 mg) m.p. 95°-96°.

Provenance & Evidence