Ethanolamine → N-[1-(3,4-dimethoxyphenyl)-2-phenylethyl]-2-hydroxy-2-(2-chloropyrid-5-yl)-ethylamine

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Reaction Steps

To a solution of α-(3,4-dimethoxyphenyl)-benzenee-thanamine (see Washburn et al., EP 0 659 737 A2 for the preparation of this compound) (257 mg, 1 mmol, 2 eq) in anhydrous acetonitrile (10 mL) is added a solution of 2-chloro-5-(2-bromoacetyl)pyridine (prepared as described in Example 3) (111 mg, 0.5 mmol) at 0° C. under a nitrogen atmosphere. The mixture is allowed to warm to room temperature and stirred for 1 h. To this mixture is added a solution of sodium borohydride (110 mg, 2.9 mmol, 5.8 eq) in abs. ethanol at room temperature. After one hour, the excess sodium borohydride is quenched with 1N HCl to pH 4.0 and then ethanol amine (0.28 mL, 4.5 mmol, 8 eq) is added. After stirring for 10 minutes, the mixture is diluted with ethyl acetate (30 mL). The organic layer is washed with brine, dried over anhydrous sodium sulfate and then concentrated. Purification by silica column gives the desired compound.

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