N-(2-aminoethyl)acetamide → HCID 19036565, compound

Participants

Reaction Steps

N-Acetylethylenediamine (2.9 g) was dissolved in 50 ml of methylene chloride under argon, treated in succession with 4.5 g of molecular sieve 4 Å and a solution of 5.7 g of 7-chloro-1,2,3,4-tetrahydro-1-oxo-2-naphthaleneacetaldehyde in 20 ml of methylene chloride and heated to reflux for 16 hours while stirring. The reaction mixture was cooled, filtered over a Celite® pad and the filtrate was freed from solvent. The crude product, 6.6 g of brown solid, 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 4.0 g (55%) of N-[2-(8-chloro-4,5-dihydro-1H-benzo[g]indol-1-yl)ethyl]acetamide; m.pt.: 144°-146° C.

Provenance & Evidence