2-Amino-1-(3-chlorophenyl)ethan-1-ol → 3-Chloro-alpha-[[[2-[4-(3-pyridylmethyloxy)phenyl]-1-methylethyl]amino]methyl]benzenemethanol

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Reaction Steps

A mixture of 1-[4-(3-pyridylmethyloxy)phenyl]propan-2-one (7.2 g) and 2-hydroxy-2-(3-chlorophenyl)ethanamine (5.1 g) was boiled under reflux with azeotropic removal of water until the reaction was complete. The solvent was evaporated, the residue dissolved in methanol (150 ml), cooled in an ice-bath and treated with sodium borohydride (5 g). After stirring for 1 hour the methanol was evaporated and the residue partitioned between ethyl acetate and water. The organic phase was washed with water, dried and evaporated to give an oil which was chromatographed on Kieselgel 60. Elution with 3% methanol in chloroform gave a yellow oil (6.4 g). Bulb to bulb distillation of this oil gave 3-chloro-β-[[[2-[4-(3-pyridylmethyloxy)phenyl]-1-methylethyl]amino]methyl]benzenemethanol b.p. 120°-130° C./0.4 mm, as a 1:1 mixture of diastereoisomers.

Provenance & Evidence