Methyl iodide → HCID 12361861, compound

Participants

Reaction Steps

To a slurry of 1 g. of sodium hydride in 20 ml. of dimethylformamide was added 9.5 g. of 3-(dimethylamino)-5-methyl-1,2,3,4-tetrahydrocarbazole (Example 245A) in 100 ml. of dimethylformamide. The mixture was stirred for one hour, 5.9 g. of methyl iodide was added to the resulting clear solution in one portion, and the solution was heated for 2 hours on a steam bath, stirred at room temperature for 1 hour, diluted in 300 ml. of water and left stand for 18 hours. The resulting solids were filtered, the filtrate was extracted with ether, the ether extract was washed with water and dried over magnesium sulfate and evaporated to dryness. The residue was combined with the solids, dissolved in ether and treated with hydrogen chloride in ethyl alcohol to give, on recrystallization from water, 3.5 g. of 3-(dimethylamino)-5,9-dimethyl-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 318°-320°C.

Provenance & Evidence