Ammonia → HCID 19095359, compound

Participants

Reaction Steps

3-Cyclohex-2-enyl-5,6,10,11-tetrahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole (1.05 g) was dissolved in 100 ml of methanol and treated with 0.2 ml of methanesulphonic acid. After the addition of 100 mg of tris(triphenylphosphine)-rhodium-(I) chloride the mixture was hydrogenated at room temperature for 24 hours. The mixture was freed from solvent, treated with 100 ml of 10% ammonia solution and extracted three times with 100 ml of methylene chloride each time. The organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 0.95 g of yellow oil, was dissolved in a 20-fold amount of ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. After concentration to a volume of about 16 ml and addition of 30 ml of ethyl acetate there separated 0.57 g of yellow crystals which were recrystallized from an ethanol/ethyl acetate mixture (1:2). There was obtained 0.39 g (37%) of 3-cyclohexyl-5,6,10,11 -tetrahydro-8-methyl-benzo[g]pyrazino[1,2-a]indole fumarate (1:1); m.pt.: 165°-167° C. (dec.).

Provenance & Evidence