Hydrazine hydrate (1:1) → (2-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}ethyl)amine

Participants

Reaction Steps

2-(2-{4-[(6-Butyl-8-quinolinyl)oxy]-1-piperidinyl}ethyl)-1H-isoindole-1,3(2H)-dione (for example, as prepared for Intermediate 30) (2.76 g, 6.03 mmol) was stirred under nitrogen in ethanol (40 ml) containing hydrazine monohydrate (commercially available, for example, from Aldrich) (0.71 ml, 15.1 mmol) at 80° C. for 2 h. The reaction was cooled with ice-water and filtered. The filter-cake was leached with ethanol and the combined filtrates were evaporated to an oil containing a white solid. This solid was mixed with DCM (about 20 ml) and filtered. The filter-cake was leached with more DCM and the combined filtrates were evaporated to give the title compound (2.07 g) as an oil: LCMS RT=2.32 min, ES+ve m/z 328 [M+H]+.

Provenance & Evidence