Benzene, 1-(chloromethyl)-2-fluoro- → N-(2-Fluorophenylmethyl)-3-hydroxy-3-phenylpropylamine

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Reaction Steps

A mixture of 3-hydroxy-3-phenylpropylamine (7.0 g, 46 mM) and 2,2,6,6-tetramethylpiperidine (7.9 ml, 46 mM) in acetonitrile (100 ml) was treated with a solution of o-fluorobenzyl chloride (6.75 g, 46 mM) in acetonitrile (10 ml). After 24 hours the resulting precipitate was removed by filtration and washed with acetonitrile (2×10 ml). The combined filtrate and washings were evaporated under reduced pressure and the residue partitioned between 2 N hydrochloric acid (50 ml) and ether (100 ml). The aqueous layer was basified by extracted with ether, the ether extracts dried and evaporated. Chromatography on Grade 3 silica using 2% methanol in chloroform as eluant followed by distillation gave the title compound (6.3 g) b.p. 156°-160° C. (0.2 mbar). Found: C, 73.9; H, 7.1; N, 5.2%; C16H18FNO requires: C, 74.1; H, 7.0; N, 5.4%.

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