Hydrochloric Acid → HCID 70374182, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 27.0 g (0.126M) of 1-[N-(2-hydroxyethyl)-N-methylaminomethyl]-1,2,3,4-tetrahydronaphthalene, a compound of Formula 12 prepared, for example, as described in Preparation 12, dissolved in 170 ml of trichlorobenzene, at ambient temperature, was added 10.0 g (0.048M) of phosphorous pentachloride. The mixture was then heated to 110° C., and 34.0 g (0.255M) of aluminum chloride was added in portions over a period of 30 minutes. The temperature was increased 200° C. and the mixture stirred for an additional 3 hours. The reaction mixture was allowed to cool 80° C., and was then carefully combined with 900 ml of approximately 12% HCl. Toluene was added and the organic layers were removed in a separatory funnel. The remaining aqueous phase was made alkaline by the addition of 50% NaOH, and the product was extracted with ethyl acetate. The ethylacetate was evaporated and the remaining crude product purified, first by column chromatography (silica gel; 5% methanol in ethyl acetate) and finally by distillation; to yield 2-methyl-1,2,3,4,8,9,10,10a-octahydronaphth[1,8-cd]azepine (bp 105°-110° C. at 0.1 mm); (HCl salt, from ethanol-hydrogen chloride, mp 185°-186° C.).

Provenance & Evidence