Sodium Hydroxide → HCID 19095432, compound

Participants

Reaction Conditions

Reaction Steps

N-[2-(5-Methyl-1H-benzo[g]indol-1-yl)ethyl]acetamide (0.3 g) was treated with 3 ml of phosphorous oxychloride under argon and the mixture was heated to 100° C. for 30 minutes. The cooled mixture was added to 250 g of ice-water and treated with 30 ml of 28% sodium hydroxide solution. The mixture was extracted once with 100 ml of methylene chloride and twice with 50 ml of methylene chloride each time, the organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 0.14 g of brown oil, was chromatographed on 10 g of aluminium oxide (neutral, III) with methylene chloride as the eluent. The crude product, 90 mg of yellow-brown, amorphous solid was dissolved in 1 ml of ethanol and 3 ml of diethyl ether and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There were obtained 58 mg (17%) of 10,11-dihydro-5,8-dimethylbenzo[g] pyrazino[1,2-a]indole fumarate (2:1); m.pt.: 184°-186° C. (dec.).

Provenance & Evidence