Sodium Carbonate → HCID 86755083, compound

Participants

Reaction Steps

N-methyl-2-phenylbenzylamine (2.57 g) was dissolved in 17 ml of N,N-dimethylformamide (DMF), followed by the addition of 1.39 g of sodium carbonate. While stirring the resulting mixture under ice cooling, a solution of 2.5 g of 1-bromo-6,6-dimethyl-2-hepten-4-yne in DMF was added dropwise. The temperature of the mixture was allowed to rise to room temperature, at which a reaction was allowed to proceed for 16 hours. After the reaction mixture was concentrated under reduced pressure, water and diethyl ether were added to subject the resulting concentrate to liquid-liquid extraction. The organic layer was collected and then dried over magnesium sulfate. The solvent was then distilled off. The residue was purified by chromatography on a silica gel (eluent:hexane/ethyl acetate=10/1), whereby trans-N-(6,6-dimethyl-2-hepten-4-yn-1-yl)-N-methyl-2-phenylbenzylamine (Compound 5) and cis-N-(6,6-dimethyl-2-hepten-4-yn-1-yl)-N-methyl-2-phenylbenzylamine (Compound 6) were obtained in amounts of 2.15 g (yield: 54.5%) and 0.73 g (yield: 18.5%), respectively. The followings are their NMR spectrum data:

Provenance & Evidence