Potassium Iodide → N-nitroso-N'-2-thenylpiperazine

HRID 2286507Notes

Reaction equation

HRID 2286507 reaction equation
Cl[CH2:2][C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.[N:8]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)=[O:9].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CC(C)=O>[N:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:2][C:3]2[S:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][CH2:11]1)=[O:9]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 21845N-NitrosopiperazineHCID 698302-(Chloromethyl)thiophene

Product 1

HCID 23461669N-nitroso-N'-2-thenylpiperazineYield 99%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2-Chloromethylthiophene (prepared as described by F. F. Blicke and J. H. Burkhatter in J. Amer. Chem. Soc., 64, 477, 1947) (5.0 g, 0.038 mole) was added to acetone (100 ml) containing N-nitrosopiperazine (5.4 g, 0.038 mole) (prepared as described in U.S. Pat. No. 2,907,767), anhydrous potassium carbonate (6.0 g, 0.04 mole) and a catalytic amount of potassium iodide (1 small crystal). The mixture was heated under reflux for 3 hours, cooled, treated with water (50 ml) evaporated to 1/3 volume and extracted with ethylacetate (3×150 ml). The combined extracts were dried (anhydrous K2CO3), filtered and evaporated in vacuo to yield N-nitroso-N'-2-thenylpiperazine (7.35 g, >99%) as a straw coloured oil.

Workup

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

Sources & evidence

ORD record
ord-8283ab0fcb6643028f4ae8fb2e56bfed
Source dataset
uspto-grants-1981_05
Patent number
US04267175

Reaction notes

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