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

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Reaction Steps

A solution of 4-amino-α-(aminomethyl)-3,5-dichlorobenzenemethanol (0.56 g,), 2-[2-[[2-[(6-bromohexyl)oxy]ethyl]thio]ethyl]pyridine (0.58 g,) and DEA (0.26 g,) in DMF (10 ml) was stirred under nitrogen for 2 h. The solvent was evaporated in vacuo and the residual oil partitioned between 8% sodium bicarbonate solution (100 ml) and dichloromethane (100 ml). The aqueous phase was re-extracted with dichloromethane (100 ml) and the combined organic phases dried and evaporated in vacuo to give an oil. Purification by FCC eluting with System G (98:2:1) gave an oil. Trituration with hexane afforded the title compound (451 mg,) as a solid m.p. 59.5°-62°. T.l.c. (System E 40:10:1) Rf 0.32.

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