Fumaric Acid → HCID 19095434, compound

Participants

Reaction Steps

3-Cyclopentyloxy-5,6,10,11-tetrahydro-8-methylbenzo[g]pyrazino[1,2-a]indole (0.8 g) was dissolved in a mixture of 50 ml of methanol and 5 ml of water under argon. The solution was treated portionwise with 0.3 g of sodium borohydride while stirring and stirred at room temperature overnight. Thereafter, the methanol was removed in a vacuum, the residue was taken up in 30 ml of methylene chloride and washed with 50 ml of 10% ammonia solution. The phases were separated and the aqueous phase was extracted twice with 30 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 0.8 g of amorphous, brown solid, was chromatographed on 30 g of silica gel with methylene chloride/methanol mixtures (50:1 to 20:1). The isolated crude product was dissolved in a 25-fold amount of hot ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There was obtained 0.34 g (31 %) of 3-cyclopentyloxy-5,6,8,9,10,11-hexahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole fumarate (2:1); m.pt.: 187°-189° C. (dec.).

Provenance & Evidence