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 upon evaporation of the solvent gave a viscous liquid which was redissolved in CH2Cl2, washed with water (3×50 mL), then brine (50 mL). The organic layers were combined, dried over Na2SO4 and the solvent evaporated, leaving an yellowish oil, which upon addition of a few drops of ACN and re-evaporated yielded the title compound (8.6 g, 35.3 mmol). 1H NMR (400 MHz, MeOD) δ ppm 4.09 (d, J=13.14 Hz, 2H) 2.70-2.85 (br. s., 2H) 2.23-2.43 (m, 1H) 1.66-1.77 (m, 2H) 1.49-1.66 (m, 2H) 1.40-1.49 (m, 9H). MS (m/z, MH−): 242.2

Provenance & Evidence