Hexane → HCID 58933201, compound

Participants

Reaction Steps

A solution of N-(1,5-dimethyl-4-hexenylidene)aniline (2.0 g) in benzene (2 ml) was added under a flow of hydrogen gas to a mixture of RuHCl(R,R—BINAP)(R,R—CYDN) (5 mg) and KOiPr (5 mg) in a Schlenk flask. The flask was then cooled to liquid nitrogen temperature, filled with H2 gas, closed and allowed to gradually warm to room temperature. The mixture was vigorously stirred for 24 hours. A 1H NMR spectrum of the reaction mixture indicated complete conversion of the imine to the amine. Hexane (10 ml) was added to the mixture, which was then eluted (hexane) through a short column of silica gel in order to remove the spent catalyst and KOiPr. Evaporation of the hexane under reduced pressure resulted in spectroscopically pure N-(1,5-dimethyl-4-hexenyl)aniline, as verified by 1H and 13C NMR.

Provenance & Evidence