Dimethylformamide → (+/-)-1-[(4-Chlorobenzyl)morpholin-2-yl]-2-(2-methoxyphenyl)-ethene oxalic acid salt

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A mixture of N-(4-chlorobenzyl)-N-(2-hydroxyethyl) amine (2.00 g, 10.8 mmol) and cis-1,4-diacetoxy-2-buten (2.78 g, 16.2 mmol), triethylamine (3.26 g, 32.3 mmol), tetrakis triphenylphosphino palladium(O) (0.31 g, 0.27 mmol) in THF (20 ml) was refluxed overnight. DMF (10 ml) was added and the THF was stripped off in vacuum. Addition of 2-iodoanisole (3.8 g, 16.2 mmol) and diisopropylethylamine (2.8 g, 21.6 mmol) was followed by heating to 130° C. overnight. Ether was added and the organics were washed twice with aqueous sodium hydroxide (1 M). Chromatography on silica gel with dichloromethane with 1% methanol as the eluent gave the free base. Dissolution in ether and precipitation with oxalic acid gave the title compound. Yield 1.0 g, 21%. mp 178-180° C.

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