N,N,N',N'-Tetramethyl-1,3-diaminopropane → Methyl 4-(((4'-chlorobiphenyl-4-yl)(cyclohexyl)methyl)amino)benzoate

Participants

Reaction Steps

Under a nitrogen atmosphere, to a mixture of (4′-chlorobiphenyl-4-yl)(cyclohexyl)methanol obtained in step B, N,N,N′,N′-tetramethyl-1,3-propanediamine (0.265 mL) and toluene (4.432 mL) was added methanesulfonyl chloride (0.124 mL) at 0° C., and the reaction mixture was stirred at room temperature for 4 hr. To the reaction mixture were added methyl 4-aminobenzoate (301 mg) and N,N-diisopropylethylamine (0.464 mL) at room temperature, and the mixture was stirred at 100° C. overnight. To the reaction mixture was added water at room temperature, the mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (382.4 mg).

Provenance & Evidence