N-(2-aminoethyl)acetamide → HCID 19036432, compound

Participants

Reaction Steps

N-Acetylethylenediamine (15.5 g) was dissolved in 300 ml of methylene chloride under argon, treated in succession with 260 g of molecular sieve 4 Å and a solution of 30.8 g of 5-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetaldehyde in 150 ml of methylene chloride and refluxed for 23 hours while stirring. The reaction mixture was cooled, filtered over a Celite® pad and the filtrate was freed from solvent. The crude product, 37.5 g of brown, amorphous material, was dissolved in a 6-fold amount of hot ethyl acetate and, after the addition of an 8-fold amount of hexane boiled briefly. There were obtained 29.4 g (74%) of N-[2-(6-chloro-4,5-dihydro-1H-benz[g]indol-1-yl)-ethyl]acetamide; m.pt.: 124°-126° C.

Provenance & Evidence