1-Ethyl-3-methylimidazolium chloride → n-Carboxymethyl-3,4,5,6-tetrahydroaniline

Participants

Reaction Steps

92 mg (0.5 mmol) of N-carboxymethyl-3-amino-1,7-octadiene and 10 mg of the ruthenium catalyst shown in the reaction scheme above, namely (tricyclohexylphosphine)-benzylidene-chloro-ruthenium-(IV) 2-[(2,6-diisopropylphenyl)imino]methyl-4-nitro-phenoxide, were dissolved in 1 ml of absolute hexane and a mixture of 290 mg (2 mmol) of 1-methyl-3-ethylimidazolium chloride and 266 mg (2 mmol) of aluminium trichloride under an argon atmosphere in a baked-out Schlenk tube. The mixture was allowed to react for 3 hours at 50° C. For the work-up, the organic phase was pipetted off and the phase comprising the ionic liquid was washed twice with 2 ml each time of hexane. The combined hexane phases were evaporated. Finally, the mixture was filtered through a very short silica gel column (0.2 cm), washed once with 1 ml of acetonitrile and evaporated. The catalyst dissolved in the ionic liquid is available for a further reaction with substrate in hexane.

Provenance & Evidence