Ethanol → HCID 12798076, compound

Participants

Reaction Steps

A solution of N-(2,3,4,9-tetrahydro-1,4-ethano-1H-carbazol-2-yl)-N-methyl-formamide (3.9 g, 0.0145 mole, described in Example 7) in 20 ml of 10% sodium hydroxide and 40 ml ethanol was refluxed under nitrogen on a steam-bath for 5 hr. The solution was evaporated to dryness and the residue was taken up in diethyl ether. The organic layer was washed (3×) with 2 N hydrochloric acid and the acidic layer was washed with diethyl ether. The aqueous layer was made basic with 25% sodium hydroxide and extracted with diethyl ether. The ether extract was washed with water, dried, evaporated to afford the title compound as a pale yellow oil (3 g): NMR (CDCl3) δ 1.0 (s, 1H), 2.32 (3, 3H), 3.75 (s, 3H) and 2.1-7.7 (m, 4H). It was chromatographed on silica gel and eluted with 5% methanol-chloroform to give a pale yellow oil (2.2 g) which was dissolved in dichloromethane and treated with a solution of hydrogen chloride in diethyl ether to form a gummy precipitate. The residue was crystallized from methanol-dichloromethane-diethyl ether to yield a greenishgray compound (2.0 g). Recrystallization from methanol-dichloromethanediethyl ether afforded the hydrochloride salt of the title compound as an off-white powder (1.95 g): mp 204°-205° C.; and Anal. Calcd for C16H20N2.HCl: C, 69.41% H, 7.65% N, 10.12% and Found: C, 69.25% H, 7.55% N, 9.89%.

Provenance & Evidence