Hydrochloric Acid → HCID 86743853, compound

Participants

Reaction Steps

A solution of 11.5 g (0.029 mol) of N-[3-(diethylamino)propyl]-4,5-diphenyl-1H-pyrazole-1-ethanamine of example 12 in 160 mL of THF was added dropwise with stirring at 0° C. under nitrogen to 240 mL of a 1M THF solution of diborane (0.024 mol). The reaction was slowly heated to reflux and allowed to reflux 18 hr. The solvent and excess diborane were stripped off in vacuo, and the residue was treated with 400 mL of 6N HCl, cautiously at first, then with heating on steambath for 1 hr. The solution was cooled, made basic with NaOH, and extracted into methylene chloride; the methylene chloride solution was dried over MgSO4 and stripped to a dark oil. The oil was dissolved in hot ethanol and a solution of 2 equivalents of fumaric acid in hot ethanol was added. The solution was chilled and 8.7 g of N-[3-(diethylamino)propyl]-4,5-diphenyl-1H-pyrazole-1-ethanamine (E)-2-butenedioate (1:2), mp 95°-100° C., was obtained by filtration.

Provenance & Evidence