Sodium Iodide → rac-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benz[e]indole

Participants

Reaction Steps

A suspension of 24.1 g (0.12 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole, 28.3 g (0.15 mol) of 2-cyclohexylethyl bromide, 26.3 g (0.19 mol) of potassium carbonate and 6.22 g (0.04 mol) of sodium iodide in 550 ml of ethyl methyl ketone was boiled at reflux for 3 days. The solid was filtered off and the solvent was distilled in a vacuum. The residue was dissolved in ethyl acetate, whereupon the solution was washed with water and sodium chloride solution and concentrated. After chromatography over silica gel (ethyl acetate-methylene chloride 1:2) there were obtained 16.1 g (43%) of rac-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benz[e]indole as a beige oil.

Provenance & Evidence