Hydrochloric Acid → 4-Amino-3,5-dichloro-alpha-[[[6-[2-(2-pyridinyl)ethoxy]hexyl]amino]methyl]benzenemethanol

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4-Amino-3,5-dichloro-α-[[(phenylmethyl)[6-[2-(2-pyridinyl)ethoxy]hexyl]amino]methyl]benzenemethanol (1.1 g) was hydrogenated over pre-reduced 10% palladium oxide on carbon (50% aqueous paste, 200 mg) in ethanol (10 ml) containing hydrochloric acid (conc. HCl/ethanol, 1:9 v/v, 4 ml). The catalyst was removed by filtration through hyflo, the solvent was evaporated and the residual oil was partitioned between 8% sodium bicarbonate (25 ml) and ethyl acetate (25 ml). The organic layer was washed with 8% sodium bicarbonate, water and brine, dried and concentrated to an orange oil which was purified by FCC eluting with System C (95:5:1→90:10:1) to give a yellow oil which was triturated with ether-hexane to give the title compound as a white solid (280 mg) m.p. 94°-96°.

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