Potassium Iodide → 1-(3-Methylbutyl)-4-nitrosopiperazine

HRID 2286511Notes

Reaction equation

HRID 2286511 reaction equation
[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4]Br.[N:7]([N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:8].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[CH3:1][CH:2]([CH3:6])[CH2:3][CH2:4][N:12]1[CH2:13][CH2:14][N:9]([N:7]=[O:8])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 78911-Bromo-3-methylbutaneHCID 11430Potassium CarbonateHCID 21845N-Nitrosopiperazine

Product 1

HCID 234616511-(3-Methylbutyl)-4-nitrosopiperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methyl-1-bromo-butane (3.94 g.), N-nitroso-piperazine (3 g.), anhydrous potassium carbonate (3.6 g.) and a small crystal of potassium iodide in dimethyl formamide was heated at 100° for 2 hours. Solvent was removed under reduced pressure and the residue dissolved in ether and water. The ether extract was separated, dried and evaporated to give an oil which was adsorbed on silica gel. Elution with ethyl acetate gave N-(3-methylbutyl)-N'-nitroso piperazine, further purified by dissolving in dilute acid, washing the acid extract with ether, basifying the acid extract and re-extracting with ether. The yield of colourless oil was 3 g (62%).

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in ether
  3. extractionThe ether extract
  4. customwas separated
  5. customdried
  6. customevaporated
  7. customto give an oil which
  8. washElution with ethyl acetate

Sources & evidence

ORD record
ord-ac059a02315d4494b662560f18c8a284
Source dataset
uspto-grants-1981_05
Patent number
US04267175

Reaction notes

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