Water → 2-Butanoyl-2-azabicyclo[2.2.1]hept-5-EN-3-one

HRID 1385572Notes

Reaction equation

HRID 1385572 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[C:3](=[O:8])[NH:2]2.N1C=CC=CC=1.[C:15](Cl)(=[O:19])[CH2:16][CH2:17][CH3:18].O>C(#N)C>[C:15]([N:2]1[C:3](=[O:8])[CH:4]2[CH2:7][CH:1]1[CH:6]=[CH:5]2)(=[O:19])[CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 8855Butyryl chlorideHCID 5486782-Azabicyclo(2.2.1)hept-5-en-3-one

Product 1

HCID 226732852-Butanoyl-2-azabicyclo[2.2.1]hept-5-EN-3-oneYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

100.3 g of (±)-2-azabicyclo[2.2.1]hept-5-en-3-one were dissolved in acetonitrile (720 ml) and pyridine (142 ml) under nitrogen. At 12° C., 141.8 g of butyryl chloride were added dropwise over the course of 1 hour. The reaction was then stirred at room temperature for 3 hours. 720 ml of water were added to the mixture, and the phases were separated. The acetonitrile was evaporated off in vacuo, and the aqueous phase was extracted 3 times with ethyl acetate (300 ml). The combined org. phases were washed with 1N HCl (350 ml), saturated NaCl (400 ml) and water (500 ml), dried with magnesium sulphate and completely evaporated. The product was purified by distillation. 107.76 g of product were obtained as a clear liquid. The yield was 85%.

Workup

  1. customthe phases were separated
  2. customThe acetonitrile was evaporated off in vacuo
  3. extractionthe aqueous phase was extracted 3 times with ethyl acetate (300 ml)
  4. washphases were washed with 1N HCl (350 ml), saturated NaCl (400 ml) and water (500 ml)
  5. dry with materialdried with magnesium sulphate
  6. customcompletely evaporated
  7. distillationThe product was purified by distillation

Sources & evidence

ORD record
ord-52a37434b52a44a496c9d25d227c80bd
Source dataset
uspto-grants-2001_07
Patent number
US06262295B1

Reaction notes

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