Water → HCID 67229211, compound

Participants

Reaction Steps

10 g of 2-chloro-5-(trifluoromethyl)pyridine and 40.5 ml of N-benzylethylenediamine are heated at 135° C. for 6 hours in a round-bottomed flask. The resulting mixture is poured into water and extracted with ethyl acetate. The extracts are dried and evaporated under vacuum; the crude product thus obtained is purified by flash chromatography. The isolated product (compound of formula (VIII)), 14 g, is dissolved in 200 ml of 2N HCl solution. 30 g of trimeric glyoxal dihydrate are added and the mixture is stirred at room temperature for 72 hours. The resulting mixture is extracted with ethyl acetate. The extracts are dried and evaporated under vacuum; the crude product thus obtained is purified by flash chromatography. The isolated product, 10 g, is dissolved in 450 ml of ethanol, followed by addition of 15 ml of a solution of isopropanol saturated with HCl and 3 g of 10% Pd/C. This mixture is reacted under a stream of hydrogen for 4 hours at a temperature of 40° C. The resulting mixture is filtered and evaporated under vacuum to give 3 g of the title compound, m.p.=205-207° C.

Provenance & Evidence