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

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Reaction Steps

Sodium borohydride (0.16 g) was added portionwise over 5 min to a solution of 1-(4-amino-3,5-dichlorophenyl)-2-[[6-[2-(2-pyridinyl)ethoxy]hexyl]amino]ethanone (0.44 g) in methanol (7 ml) at 0°-5° with stirring. After 1.5 h, the solution was evaporated in vacuo and the residue partitioned between water (60 ml) and ethyl acetate (100 ml). The organic phase was dried and evaporated in vacuo to a gum which was purified by FCC eluting with System C (90:10:1) to afford a product, which was triturated with hexane (2 ml) to give the title compound as a colourless powder (47 mg), m.p. 94.5°-96.5°, t.l.c. (System A 39:10:1) Rf 0.44.

Provenance & Evidence