tert-Butyl carbazate → Tert-butyl 2-(1-methylpiperidin-4-ylidene)hydrazinecarboxylate

HRID 2109260Notes

Reaction equation

HRID 2109260 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[C:9]([NH:16][NH2:17])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>>[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[N:17][NH:16][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 70091tert-Butyl carbazateHCID 740491-Methyl-4-piperidone

Product 1

HCID 21097379Tert-butyl 2-(1-methylpiperidin-4-ylidene)hydrazinecarboxylateYield 32%

Procedure

A solution of 11.2 g (99.0 mmol) of 1-methyl-piperid-4-one and 13.0 g (100 mmol) of Boc-hydrazine in 150 mL of hexanes was refluxed for 30 minutes. The hot solution was dried over MgSO4, filtered, and allowed to cool. The resulting crystals were isolated and recrystallized from Et2O to provide 7.2 g of tert-butyl N′-(1-Methyl-piperidin-4-ylidene)-hydrazinecarboxylate as a white solid.

Workup

  1. dry with materialThe hot solution was dried over MgSO4
  2. filtrationfiltered
  3. temperatureto cool
  4. customThe resulting crystals were isolated
  5. customrecrystallized from Et2O

Sources & evidence

ORD record
ord-bd36b320da88410b94f7e7655875b826
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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