Sulfuric acid magnesium salt (1:1) → Tert-butyl 2-(1-tert-butylpiperidin-4-ylidene)hydrazinecarboxylate

HRID 1530655Notes

Reaction equation

HRID 1530655 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[O-]S([O-])(=O)=O.[Mg+2].[NH:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH2:19]>C(Cl)Cl>[C:1]([N:5]1[CH2:10][CH2:9][C:8](=[N:19][NH:18][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 70091tert-Butyl carbazateHCID 738401-tert-Butyl-4-piperidone

Product 1

HCID 48916874Tert-butyl 2-(1-tert-butylpiperidin-4-ylidene)hydrazinecarboxylateYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butylpiperidin-4-one (1.0 g, 6.5 mmol) in DCM (20 mL) was added MgSO4 (1.5 g, 13 mmol) and tert-butyl hydrazinecarboxylate (0.7 g, 5.3 mmol). The reaction mixture was heated to reflux overnight. The solid was filtered off and the filtrate was concentrated. The residue was purified by silica gel chromatography eluting with EtOAc/petroleum ether (1:20) to give tert-butyl 2-(1-tert-butylpiperidin-4-ylidene)hydrazinecarboxylate (1.2 g, 84% yield) as a colorless oil. LCMS (ESI) m/z: 270.3 [M+H+].

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. filtrationThe solid was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with EtOAc/petroleum ether (1:20)

Sources & evidence

ORD record
ord-d7528fa5e41043f888fef843f40daa8b
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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