Reaktion #1119451

Reaktionsgleichung

1-[N-(2-hydroxyethyl)-N-methylaminomethyl]-1,2,3,4-tetrahydronaphthalene

HCl

phosphorous pentachloride

aluminum chloride

trichlorobenzene

→

2-methyl-1,2,3,4,8,9,10,10a-octahydronaphth[1,8-cd]azepine

Lösungsmittel

Toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeas described in Preparation 12
2. 2
   TemperaturThe temperature was increased 200° C.
3. 3
   Temperaturto cool 80° C.
4. 4
   Sonstigethe organic layers were removed in a separatory funnel
5. 5
   workup.ADDITIONby the addition of 50% NaOH
6. 6
   Extraktionthe product was extracted with ethyl acetate
7. 7
   SonstigeThe ethylacetate was evaporated
8. 8
   workup.DISTILLATIONthe remaining crude product purified, first by column chromatography (silica gel; 5% methanol in ethyl acetate) and finally by distillation

Vorschrift

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.).

Quelle