Dimethylamine → 3-(4-Chlorophenyl)-N,N-dimethyl-3-(pyridin-3-yl)prop-2-en-1-amine

Participants

Reaction Conditions

Reaction Steps

Palladium acetylacetonate (9.3 mg, 0.03 mmol), 1,2-bis-(diphenylphosphino)ethane (17.5 mg, 0.04 mmol) and 3-acetoxy-3-(4-chlorophenyl)-3-(3-pyridyl)-1-propene (0.211 g, 0.73 mmol) was dissolved in tetrahydrofuran (2.2 ml) at room temperature under nitrogen. A solution of dimethylamine in tetrahydrofuran (3.2 ml of a 2.5 M solution) was added. The resulting solution was warmed to 55° C. and allowed to react for 1 h and 40 min. Evaporation of the solvent and work-up by preparative TLC (SiO2, ethyl acetate/hexane/triethylamine 49/49/2) gave 0.158 g (79%) of a Z/E mixture of the title compound. The Z/E ratio was determined by 1H NMR to 55/45.

Provenance & Evidence