Fumaric Acid → HCID 19095322, compound

Participants

Reaction Steps

3-n-Butyl-5,6,10,11-tetrahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole (0.47 g) was dissolved in a mixture of 20 ml of methanol and 2 ml of water under argon. The solution was treated portionwise with 0.18 g of sodium borohydride while stirring and stirred at room temperature for 4 hours. Thereafter, the methanol was removed in a vacuum and the residue was stirred with 50 ml of ether and 20 ml of 10% ammonia solution. The phases were separated and the aqueous phase was extracted once with 50 ml of ether. The organic phases were combined, dried with MgSO4 and freed from solvent. The crude product, 0.47 g of yellowish 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 (19%) of 3-n-butyl-5,6,8,9,10,11-hexahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole fumarate (2:1); m.pt.: 174°-176° C. (dec.).

Provenance & Evidence