Ethanol → HCID 12798076, compound

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%.

1. customThe solution was evaporated to dryness
2. washThe organic layer was washed (3×) with 2 N hydrochloric acid
3. washthe acidic layer was washed with diethyl ether
4. extractionextracted with diethyl ether
5. extractionThe ether extract
6. washwas washed with water
7. customdried
8. customevaporated

ORD record

ord-6d2a4b0bef1f46069938dbe220b20758

Source dataset

uspto-grants-1981_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04304772