Neo-Gilurtymal, Giulini ,W. Germany,1973
1 g of ajmaline was dissolved in 4 cc of chloroform, and 1 cc of allyl bromidewas added to the resulting solution. The reaction mixture thus obtained was allowed to stand for 24 hours at room temperature. Thereafter, the clear reaction solution was briefly cooled to a temperature below 0°C, whereby crystallization set in. The crystals were filtered off and were then recrystallized from a mixture of absolute methanol and absolute ether. The purified colorless crystalline product was identified to be N-(b)-allyl-ajmalinium-bromide having a melting point of 252°C to 254°C.
75 g of N-(b)-n-propyl-ajmalinium-bromide were suspended in 3 liters of an aqueous saturated solution of sodium bicarbonate, and the suspension was admixed with 3 liters of chloroform. The resulting mixture was vigorously stirred for six to eight hours. Thereafter, the chloroform phase was separated and evaporated to dryness. 68 g of a yellow syrup remained as a residue. The aldehyde base was dissolved in about 150 cc of acetone and, while stirring and cooling on an ice bath, the solution was slowly admixed with a solution of 25 g of tartaric acid in 2 liters of acetone. The fine white precipitate formed thereby was separated by vacuum filtration, washed with ether and dried. The raw product, weighing 80 g, was recrystallized once from a mixture of ethanol and ether, yielding 50 g of N-(b)-n-propyl-ajmalinium hydrogen tartrate having a melting point of 149°C to 152°C (decomposition).
