Hexane → 4-Amino-3-chloro-alpha-[[[6-(2-pyridinylethoxy)hexyl]amino]methyl]-5-(trifluoromethyl)benzenemethanol

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A solution of 4-amino-3-chloro-α-[[(phenylmethyl)[6-(2-pyridinylethoxy)hexyl]amino]methyl]-5-(trifluoromethyl)benzenemethanol (1.50 g) in absolute ethanol (10 ml) and conc. hydrochloric acid/ethanol (1:9 v/v, 2.48 ml) was hydrogenated over pre-reduced 10% palladium oxide on charcoal (50% aqueous, 300 mg) in absolute ethanol (10 ml). The mixture was filtered through hyflo and evaporated in vacuo to give an oil. Purification by FCC eluting with toluene-ethanol- triethylamine (95:5:1) gave a pink oil. Trituration with hexane afforded the title compound as a pale orange solid (0.87 g), m.p. 51.5°-53°.

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