Hydrazine hydrate (1:1) → HCID 178423887, compound

HRID 721984

Reaction equation

HRID 721984 reaction equation
C[N:2]([CH:4]=[C:5]1[CH2:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]1=O)C.O.[NH2:14]N>C(O)C>[CH3:10][C:7]1([CH3:11])[C:6]2[C:5](=[CH:4][NH:2][N:14]=2)[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 695835902-[(Dimethylamino)methylene]-5,5-dimethylcyclopentanone

Product 1

HCID 178423887HCID 178423887, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[(dimethylamino)methylene]-5,5-dimethylcyclopentanone (12.5 g, 75 mmol) in ethanol (100 mL) at room temperature was added hydrazine hydrate (4 mL, 82.3 mmol). The reaction mixture was heated at reflux overnight. It was then cooled to room temperature and concentrated. Water (700 mL) was added to the residue, and the resulting solution was extracted twice with diethyl ether (2×250 mL). The organic extracts were combined, dried over MgSO4 and concentrated to give the title compound as an oil (10.5 g). 1H NMR indicated the oil to be ˜60% pure. It was used directly for Step C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated
  4. additionWater (700 mL) was added to the residue
  5. extractionthe resulting solution was extracted twice with diethyl ether (2×250 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f657392d3ec74be3a5f9a13e2dda1db6
Source dataset
uspto-grants-2006_11
Patent number
US07138361B2

Linked notes

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