Stannous Chloride → HCID 70188090, compound

Participants

Reaction Steps

7.72 g of N-[(4-methoxyphenyl)-(3-nitrophenyl)methyl]-N-[(R)-1-p-tolylethyl]amine [prepared as described in step (a) above] were dissolved in 150 ml of ethanol. Tin (II) chloride (15.6 g) was added to the resulting solution, which was then heated under reflux for 3 hours. The reaction mixture was allowed to cool, and the ethanol was distilled off. The residue was dissolved in ethyl acetate. The organic solution was washed with a 1N aqueous solution of sodium hydroxide and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. The yellow oil thus obtained was purified by chromatography through a silica gel column using an 8:1 by volume mixture of toluene and tetrahydrofuran as eluant, to obtain 1.43 g and 0.78 g of isomer A and isomer B of the title compound, respectively, each as a pale yellow oil.

Provenance & Evidence