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

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.

1. customto react for 3 hours at 50° C
2. washwas washed twice with 2 ml each time of hexane
3. customThe combined hexane phases were evaporated
4. filtrationFinally, the mixture was filtered through a very short silica gel column (0.2 cm)
5. washwashed once with 1 ml of acetonitrile
6. customevaporated
7. dissolutionThe catalyst dissolved in the ionic liquid
8. customis available for a further reaction with substrate in hexane

ORD record

ord-a7eb0473c5b84420a42ca0e8460f7f59

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06756500B1