Sodium hydride → HCID 44210827, compound

Participants

Reaction Steps

1-Methyl-1H-indole-3-carboxamide oxime (C. J. Swain et al, J.Med. Chem, 1991, 34, 147)(0.250 g, 1.33 mmol) was dissolved in dry THF (8 ml) with stirring and treated with ground 4A° molecular sieves (1 g), under nitrogen. After 30 minutes sodium hydride (80% dispersion in mineral oil) (0.044 g, 1.46 mmol) was added. The mixture was then heated to reflux, after 30 minutes, the mixture was allowed to cool momentarily, and a solution of ethyl-4-N-methylbutylaminobutyrate (0.293 g, 1.46 mmol) in dry THF (2 ml) was added. The mixture was then heated to reflux. After 6 h, the reaction mixture was allowed to cool, and was then filtered. The filter pad was then washed with THF (2×) and the filtrate evaporated under reduced pressure. The residue was then purified by silica-gel chromatography, eluting with ethyl acetate/methanol 20:1 to afford the title compound as a colourless oil (0.243 g, 56%), which was converted to its hydrochloride salt, m.pt, 174°-175° C.

Provenance & Evidence