Octane → HCID 15663655, compound

HRID 275371Notes

Reaction equation

HRID 275371 reaction equation
CCC[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[NH:9]1[CH:13]=[N:12][CH:11]=[N:10]1.[Na].[NH:15]1[CH:19]=[CH:18]N=N1>CN(C=O)C.CO.C(Cl)Cl>[N:9]1([CH:7]2[CH:6]3[CH2:5][CH2:4][N:15]([CH2:19][CH2:18]3)[CH2:8]2)[CH:13]=[N:12][CH:11]=[N:10]1

Participants

7

Reactant 4

HCID 356OctaneHCID 92571H-1,2,4-TriazoleHCID 5360545SodiumHCID 178418936HCID 178418936, compound

Product 1

HCID 15663655HCID 15663655, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of (±)3-methanesulphonyloxy-1-azabiyclo[2.2.2]octane (1.3 g; 6.3 mmol) in dry DMF (20 mL) was added 1,2,4-triazole, sodium salt (1.5 g; 21 mmol). The resulting mixture was refluxed for 2 hours. The reaction mixture was cooled to room temperature and concentrated to dryness. The residue was taken up into 1M Na2CO3 and extracted into CH2Cl2 (3×50 mL). The organics were combined, dried (Na2SO4), filtered, and evaporated to yield 0.57 g of a crude yellow oil. MPLC (Al2O3 ; 2% MeOH/CH2Cl2) provided two fractions, the first containing a byproduct and the second containing the triazole. Yield 300 mg (27%).

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hours
  2. concentrationconcentrated to dryness
  3. extractionextracted into CH2Cl2 (3×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto yield 0.57 g of a crude yellow oil
  8. additionthe first containing a byproduct

Sources & evidence

ORD record
ord-809f6d3390034b38a84112487825608a
Source dataset
uspto-grants-1995_02
Patent number
US05393767

Reaction notes

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