Dichloromethane → HCID 21399512, compound

Participants

Reaction Steps

5.0 g. (13.3 mmoles) of 1-n-butyl-2,3,4,6,7,12-hexahydro-indolo(2,3 -a)quinolizinium perchlorate are suspended in 50 ml. of dichloromethane, and 50 ml. of distilled water and 10 ml. of 2 n sodium hydroxide are added to the suspension under constant stirring in argon atmosphere. The reaction mixture is stirred for 10 minutes, thereafter the organic phase is separated, and dried over anhydrous potassium carbonate. The drying agent is filtered off, 5.0 ml. (71 mmoles) of freshly distilled acrylonitrile are added to the filtrate, the mixture is flushed with argon, and allowed to stand at room temperature for 3 days. Thereafter the reaction mixture is evaporated in vacuo, the red oily residue is dissolved in 5 ml. of methanol, and the solution is acidified to pH = 6 with 70% perchloric acid. The crystallization of the product is initiated by scraping the wall of the flask. The flask is put into refrigerator. The separated yellow crystals are filtered off, washed with cold methanol, and the obtained 4.20 g. of product (m.p.: 215-220° C) are recrystallized from 5-fold volume of methanol. 3.70 g. (64.1 %) of 1-n-butyl-1-(2-cyanoethyl)- 1,2,3,4,6,7-hexahydro- 12H-indolo(2,3 -a)quinolizinium perchlorate are obtained in the form of yellow needles; m.p.: 224-226° C.

Provenance & Evidence