Water → 3-(5-Cyclohexylpentyn-1-yl)aniline

Participants

Reaction Steps

Under a nitrogen atmosphere, a mixture of 4.4 mL (0.037 mole) of 3-iodoaniline, 6.5 grams (0.043 mole) of 1-cyclohexyl-4-pentyne, 0.3 gram (catalyst) of bis(triphenylphosphine)palladium(II) chloride, 0.7 gram (catalyst) of copper(I) chloride, and 20.4 mL (0.146 mole) of triethylamine in 100 mL of acetonitrile was stirred at ambient temperature for about 18 hours. After this time the reaction mixture was poured into 200 mL of water, and this mixture then was extracted with three 100 mL portion of diethyl ether. The combined extracts were washed with three 100 mL portions of aqueous 10% citric acid solution and then with one 100 mL portion of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel, using 10% methylene chloride in diethyl ether as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding 11.0 grams of 3-(5-cyclohexylpentyn-1-yl)aniline that was about 91% pure. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence