Triethylamine → 3-(1-Oxo-2-propenyl)-3-azabicyclo[3.2.2]-nonane

HRID 5499

Reaction equation

HRID 5499 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[CH:6]12[CH2:14][CH2:13][CH:10]([CH2:11][CH2:12]1)[CH2:9][NH:8][CH2:7]2.C(N(CC)CC)C>C(OCC)C>[O:4]=[C:1]([N:8]1[CH2:9][CH:10]2[CH2:13][CH2:14][CH:6]([CH2:12][CH2:11]2)[CH2:7]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 92403-Azabicyclo[3.2.2]nonaneHCID 13140Acryloyl chloride

Product 1

HCID 149865713-(1-Oxo-2-propenyl)-3-azabicyclo[3.2.2]-nonane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of acryloyl chloride (4.05 ml, 0.05 mole) in 50 ml of ethyl ether was added with stirring to a cold mixture of 3-azabicyclo[3.2.2]nonane (6.26 g, 0.05 mole) and triethylamine (15.3 ml, 0.11 mole) in 250 ml of ethyl ether. The ice bath was removed and the reaction was allowed to warm to room temperature and stirred for 72 hours. The resulting white material was filtered and washed well with ethyl ether and ethyl acetate. The solvent was removed on a rotary evaporator and the residue taken up in ethyl ether, hexane added and the solution chilled. The remaining small amount of insoluble material was filtered and the solvent evaporated, leaving the product as an oil. The structure was confirmed by NMR.

Workup

  1. customThe ice bath was removed
  2. filtrationThe resulting white material was filtered
  3. washwashed well with ethyl ether and ethyl acetate
  4. customThe solvent was removed on a rotary evaporator
  5. additionhexane added
  6. temperaturethe solution chilled
  7. filtrationThe remaining small amount of insoluble material was filtered
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-a4fca27471be4fcab54d8e506201a961
Source dataset
uspto-grants-1993_09
Patent number
US05244899

Linked notes

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