Water → HCID 69272967, compound

HRID 750421Notes

Reaction equation

HRID 750421 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]1([CH2:21][C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>C(#N)C>[C:15]1([CH2:21][C:22]([C:1]23[CH2:7][CH:4]([CH:5]=[CH:6]2)[C:3](=[O:8])[NH:2]3)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7679Phenylacetyl chlorideHCID 5486782-Azabicyclo(2.2.1)hept-5-en-3-one

Product 1

HCID 69272967HCID 69272967, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

33.4 g of (±)-2-azabicyclo[2.2.1]hept-5-en-3-one were dissolved in acetonitrile (240 ml) and pyridine (48.3 ml) under nitrogen. At 12° C., 68.6 g of phenylacetyl chloride were added dropwise over the course of 30 minutes. The mixture was then stirred at room temperature for 3.5 hours. 240 ml of water were added to the mixture. The acetonitrile was evaporated off in vacuo, and the aqueous phase was extracted 3 times with ethyl acetate (150 ml). The combined org. phases were washed with 1N HCl (150 ml), saturated NaCl (150 ml) and water (150 ml), dried with magnesium sulphate and completely evaporated. The crude product was filtered through silica gel (hexane:ethyl acetate=1:1). 68.34 g of the crude product were obtained as a yellow oil.

Workup

  1. customThe acetonitrile was evaporated off in vacuo
  2. extractionthe aqueous phase was extracted 3 times with ethyl acetate (150 ml)
  3. washphases were washed with 1N HCl (150 ml), saturated NaCl (150 ml) and water (150 ml)
  4. dry with materialdried with magnesium sulphate
  5. customcompletely evaporated
  6. filtrationThe crude product was filtered through silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-f03e42963a8f49cb98e19a2abc411600
Source dataset
uspto-grants-2008_07
Patent number
US07405065B2

Reaction notes

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