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

HRID 2088675Notes

Reaction equation

HRID 2088675 reaction equation
[N:1]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH:4]([C:7](OCC)=[O:8])[CH2:3][CH2:2]1.O.[NH2:20][NH2:21]>C(O)C>[NH:20]([C:7]([CH:4]1[CH2:5][CH2:6][N:1]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:2][CH2:3]1)=[O:8])[NH2:21]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.0 g (38.9 mmol) of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate were initially charged in 35 ml of ethanol, and 3.8 ml (3.90 g, 78 mmol) of hydrazine hydrate were added with stirring. The mixture was stirred at reflux for 9 h. The reaction mixture was cooled to RT, 1.9 ml (39 mmol) of hydrazine hydrate were added and the reaction solution was stirred at reflux for another 24 h. The solvent was concentrated, ethanol (50 ml) was added and the mixture was concentrated again. Diethyl ether (150 ml) was added, and the mixture was stirred in an ultrasonic bath for 5 min. The product was filtered off and dried. This gave 9.20 g (97% of theory) of the product.

Workup

  1. stirringThe mixture was stirred
  2. temperatureat reflux for 9 h
  3. stirringthe reaction solution was stirred
  4. temperatureat reflux for another 24 h
  5. concentrationThe solvent was concentrated
  6. additionethanol (50 ml) was added
  7. concentrationthe mixture was concentrated again
  8. additionDiethyl ether (150 ml) was added
  9. stirringthe mixture was stirred in an ultrasonic bath for 5 min
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-892615ca9dad49a4a70899246be2ca25
Source dataset
uspto-grants-2013_05
Patent number
US08436003B2

Reaction notes

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