Reaktion #1196406

Reaktionsgleichung

triethylamine

dimethylcarbamoyl chloride

rac-cis-1-[5-(6-hydroxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-3-yl)pentyl]-4,4-dimethylpiperidine-2,6-dione

→

rac-cis-3-[5-(4,4-dimethyl-2,6-dioxopiperidin-1-yl)pentyl]-2,3,3a, 4,5,9b-hexahydro-1H-benzo[e]indol-6-yl dimethylcarbamate hydrochloride

Ausbeute 80.4%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling the organic phase
2. 2
   Waschenwas washed in succession with water, sodium bicarbonate solution and water
3. 3
   Trocknendried over magnesium sulphate
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe brown oil obtained (6.3 g)
6. 6
   Sonstigewas chromatographed over a 30-fold amount of silica gel with methylene chloride/ethyl acetate 1:1
7. 7
   SonstigeAfter crystallization from ethyl acetate/ether there

Vorschrift

5.0 g (12.54 mmol) of rac-cis-1-[5-(6-hydroxy-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-3-yl)pentyl]-4,4-dimethylpiperidine-2,6-dione were dissolved in 250 ml of toluene, treated with 2.67 g (3.7 ml; 26.4 mmol) of triethylamine, 1.62 g (1.4 ml, 15.4 mmol) of dimethylcarbamoyl chloride and 250 mg of 4-dimethylaminopyridine and stirred overnight in an oil bath at an oil bath temperature of 110°. After cooling the organic phase was washed in succession with water, sodium bicarbonate solution and water, dried over magnesium sulphate and evaporated. The brown oil obtained (6.3 g) was chromatographed over a 30-fold amount of silica gel with methylene chloride/ethyl acetate 1:1 and the purified base (5.9 g of pale yellow oil) was converted into the hydrochloride in the usual manner. After crystallization from ethyl acetate/ether there were obtained 5.1 g (80%) of rac-cis-3-[5-(4,4-dimethyl-2,6-dioxopiperidin-1-yl)pentyl]-2,3,3a, 4,5,9b-hexahydro-1H-benzo[e]indol-6-yl dimethylcarbamate hydrochloride in the form of yellowish crystals of m.p. 133°-135° (dec.).

Quelle