Allyl bromide → HCID 13023230, compound

Participants

Reaction Steps

A solution of 2 g. of 4a-phenyl-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindine in 30 ml. of N,N-dimethylformamide containing 1.23 g. of sodium bicarbonate was stirred at 25° C. while 1.23 g. of 2-propenyl bromide was added in one portion. The reaction mixture was stirred and heated at reflux for four hours. After being cooled to room temperature, the reaction mixture was filtered and concentrated to an oil under reduced pressure. The residual oil was dissolved in 300 ml. of diethyl ether. The ethereal solution was washed with water, dried, and the solvent was then removed by evaporation under reduced pressure, thus providing 4a-phenyl-2-(2-propenyl)-2,3,4,4a,5,6,7,7a-octahydro-1H-2-pyrindine as an oil. The oil so formed was dissolved in 150 ml. of fresh diethyl ether, and hydrogen bromide gas was bubbled through the ethereal solution. The precipitated salt was collected by filtration and recrystallized from diisopropyl ether and isopropanol to afford 1.3 g. of 4a-phenyl-2-(2-propenyl)-2,3,4,4a,5,6,7,7a-octahydro-1H- 2-pyrindinium bromide. M.P. 185°-187° C.

Provenance & Evidence