Acetone → 1-Ethyl-4-nitrosopiperazine

HRID 2286503Notes

Reaction equation

HRID 2286503 reaction equation
[CH2:1](I)[CH3:2].CC(C)=O.[N:8]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:9].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:14]([N:13]1[CH2:2][CH2:1][N:10]([N:8]=[O:9])[CH2:11][CH2:12]1)[CH3:15]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 21845N-Nitrosopiperazine

Product 1

HCID 125546241-Ethyl-4-nitrosopiperazineYield 103.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl iodide (8.13 g, 0.052 mole) was added to acetone (80 ml) containing N-nitroso piperazine (6.0 g, 0.052 mole) (prepared as described in U.S. Pat. No. 2,907,767) and anhydrous potassium carbonate (7.3 g, 0.052 mole). The mixture was heated under reflux for 24 hours, cooled, treated with water (50 ml) evaporated to 1/2 volume and extracted with ether (3×150 ml). The combined extracts were dried (K2CO3) filtered and evaporated in vacuo to yield N-ethyl-N'-nitrosopiperazine (7.71 g, 98%), as a straw coloured oil.

Workup

  1. customprepared
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 24 hours
  4. temperaturecooled
  5. customevaporated to 1/2 volume
  6. extractionextracted with ether (3×150 ml)
  7. dry with materialThe combined extracts were dried (K2CO3)
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-ca53af96c55a4b3ebfd9f2a20a29081c
Source dataset
uspto-grants-1981_05
Patent number
US04267175

Reaction notes

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