Formaldehyde → HCID 19095396, compound

Participants

Reaction Steps

36% aqueous formaldehyde solution (1.4 ml) was added under argon to a solution of 3.7 g of 1-(2-aminoethyl)-4,5-dihydro-1H-benzo[g]indole in 70 ml of ethanol. The reaction solution was stirred under reflux for 2 hours, subsequently cooled and freed from solvent. The residue was chromatographed on 250 g of silica gel with methylene chloride/methanol (49:1) as the eluent. 1.3 g of a total of 2.8 g of product were dissolved in a 20-fold amount of hot ethanol and treated while hot with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. The precipitated solid was boiled in a 150-fold amount of methanol, filtered while hot and concentrated to a 60-fold amount of solvent. There were obtained 1.2 g (53%) of 5,6,8,9,10,11-hexahydrobenzo[g]pyrazino[1,2-a]indole fumarate (2:1); m.pt.: 183°-184° C. (dec.).

Provenance & Evidence