Toluene → HCID 86736363, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5.0 g. of dl-trans-1-oxo-5a-(3-methoxyphenyl)-decahydrocyclopent[c]azepine in 40 ml. of anhydrous toluene was added dropwise over thirty minutes to a stirred solution of 1.2 g. of sodium amide in 40 ml. of anhydrous toluene. The reaction mixture was heated at reflux for four hours, and then cooled to 25° C. and stirred while a solution of 4 g. of methyl iodide in 40 ml. of toluene was added in one portion. The reaction mixture was next heated to reflux and stirred for thirteen hours. After cooling the reaction mixture again to 25° C., 100 ml. of water was added dropwise over fifteen minutes. The aqueous layer was then separated, and the organic layer was washed with water, dried, and the solvent was removed by evaporation under reduced pressure to provide 5.3 g. of predominantly dl-cis-1-oxo-2-methyl-5a-(3-methoxyphenyl)-decahydrocyclopent[a]azepine. The product so formed was recrystallized three times from diisopropyl alcohol to afford pure dl-cis-1-oxo-2-methyl-5a-(3-methoxyphenyl)-decahydrocyclopent[ c]azepine. M.P. 103°-104° C.

Provenance & Evidence