N-(2-aminoethyl)acetamide → HCID 19095277, compound

Participants

Reaction Steps

N-Acetylethylenediamine (8.1 g) was dissolved in 150 ml of methylene chloride under argon, treated in succession with 140 g of molecular sieve 4 Å and a solution of 14.5 g of 1,2,3,4-tetrahydro-4-methyl-1-oxo-2-naphthaleneacetaldehyde in 100 ml of methylene chloride and heated to reflux for 18 hours while stirring. The reaction mixture was cooled, filtered over a Celite® pad and the filtrate was freed from solvent. The crude product, 19.4 g of dark brown oil, was chromatographed on 300 g of silica gel with ethyl acetate as the eluent. The product, 14.2 g of yellow-brown oil, was dissolved in 200 ml of ethanol, boiled with 0.7 g of Norite® and, after fitration and removal of the solvent, yielded 13.9 g (72%) of N-[2-(4,5-dihydro-5-methyl-1H-benzo[g]indol-1-yl)ethyl]acetamide which was processed without further purification.

Provenance & Evidence