Hydrochloric Acid → 3-{[1-(3,4-Difluorophenyl)ethylamino]-(3-methoxyphenyl)methyl}-4-methoxyphenylamine

Participants

Reaction Steps

810 mg of N-[1-(3,4-difluorophenyl)ethyl]-N-[(2-methoxy-5-nitrophenyl)-(3-methoxyphenyl)methyl]amine [prepared as described in step (a) above] and 1.43 g of tin (II) chloride were added to 20 ml of a 1:1 by volume mixture of concentrated hydrochloric acid and ethanol, and then the mixture was heated under reflux for 2 hours. The reaction mixture was adjusted to a weakly alkaline pH by the addition of excess sodium hydroxide, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then distilled under reduced pressure to remove the solvent. The residue was separated and purified by reverse phase HPLC [acetonitrile: acetate buffer (water:acetic acid:triethylamine=1000:2:2)=50:50], to obtain 235 mg of isomer A of the title compound as a yellow oil. The isomer mixture was purified further by chromatography through a silica gel column using a 1:1 by volume mixture of cyclohexane and ethyl acetate as the eluant, to obtain 187 mg of isomer B as a yellow oil.

Provenance & Evidence