Hydrazine hydrate (1:1) → tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate

Participants

Reaction Steps

To a stirred solution of 1-tert-butyl 4-ethylpiperidine-1,4-dicarboxylate (10 g, 38.9 mmol, 1.0 eq) in EtOH (100 mL) was added hydrazine hydrate (18.67 g, 389 mmol, 10 eq.) and the mixture was refluxed for 8 h. The reaction was cooled to room temperature and evaporation of the solvent gave a viscous liquid which was dissolved in CH2Cl2, washed with water (3×50 mL) then brine (50 mL). The organic layers were combined, dried over Na2SO4, the solvent evaporated leaving a yellowish oil, which upon addition of a few drops of acetonitrile and re-evaporation, yielded the title compound (8.6 g, 35.3 mmol) MS (m/z, MH−): 242.2.

Provenance & Evidence