Hydrochloric Acid → HCID 70374182, compound

Temperature

110 °C

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.).

1. customas described in Preparation 12
2. temperatureThe temperature was increased 200° C.
3. temperatureto cool 80° C.
4. customthe organic layers were removed in a separatory funnel
5. additionby the addition of 50% NaOH
6. extractionthe product was extracted with ethyl acetate
7. customThe ethylacetate was evaporated
8. distillationthe remaining crude product purified, first by column chromatography (silica gel; 5% methanol in ethyl acetate) and finally by distillation

ORD record

ord-02264f5dd95c40d4ba478f944238b914

Source dataset

uspto-grants-1990_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04957914