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

HRID 222244Notes

Reaction equation

HRID 222244 reaction equation
C([C:3]1([C:16]([O-:18])=O)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)C.O.[NH2:20][NH2:21]>C(O)C>[NH:20]([C:16]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=[O:18])[NH2:21]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 263398931-tert-Butyl 4-ethylpiperidine-1,4-dicarboxylate

Product 1

HCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-tert-butyl 4-ethylpiperidine-1,4-dicarboxylate (21 g), hydrazine monohydrate (40 mL), and ethanol (200 mL) was heated and refluxed for 22 hours. After leaving to be cooled, the solvent was evaporated under reduced pressure, to the residue were added saturated brine and ethyl acetate, and the organic phase was separated. The organic phase was dried over magnesium sulfate and the solvent was evaporated under reduced pressure. To the residue was added diisopropyl ether, followed by stirring for 1 hour, and the resulting solid was collected by filtration and dried under reduced pressure to obtain tert-butyl 4-(hydrazinocarbonyl)piperidine-1-carboxylate (17.8 g).

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 22 hours
  3. customAfter leaving
  4. temperatureto be cooled
  5. customthe solvent was evaporated under reduced pressure, to the residue
  6. additionwere added saturated brine and ethyl acetate
  7. customthe organic phase was separated
  8. dry with materialThe organic phase was dried over magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. additionTo the residue was added diisopropyl ether
  11. filtrationthe resulting solid was collected by filtration
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-3e590f2b72cd459e8fe8cb50eb4cd178
Source dataset
uspto-grants-2012_06
Patent number
US08207199B2

Reaction notes

Loading…