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

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Reaction Steps

4-Amino-3,5-dichloro-α-oxobenzeneacetaldehyde (0.56 g) and 6-[2-(2-pyridinyl)ethoxy]hexanamine (0.40 g) were dissolved in benzene (10 ml) and heated under reflux for 1 h using a Dean-Stark water trap. The solution was cooled, evaporated in vacuo and the residue dissolved in methanol (10 ml). Sodium borohydride (0.38 g) was added portionwise at 0°-5° over 0.5 h with stirring. The solution was allowed to stand overnight then evaporated in vacuo. The residue was partitioned between water (50 ml) containing 2N sodium carbonate (4 ml) and ethyl acetate (60 ml). The organic phase was dried, evaporated in vacuo and the residue purified by FCC eluting with System C (90:10:1) to afford a gum. Trituration with hexane gave the title compound (85 mg) as a colourless powder m.p. 93°-96°, t.l.c. (System A 39:10:1) Rf 0.44.

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