Fumaric Acid → HCID 19095318, compound

Participants

Reaction Steps

3-Cyclohexyl-5,6,10,11-tetrahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole (0.34 g) was dissolved in a mixture of 15 ml of methanol and 1,5 ml of water under argon. The solution was treated portionwise with 0.15 g of sodium borohydride while stirring and stirred at room temperature for 3 hours. Thereafter, the methanol was removed in a vacuum and the residue was stirred with 20 ml of ether and 20 ml of 10% ammonia solution. The phases were separated and the aqueous phase was extracted twice with 20 ml of ether each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The crude product, 0.35 g of colourless oil, was dissolved in a 20-fold amount of ethanol and boiled briefly with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 0.11 g (27%) of 3-cyclohexyl-5,6,8,9,10,11-hexahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole fumarate (2:1); m.pt.: 199°-202° C. (dec.).

Provenance & Evidence