Water → HCID 22748827, compound

HRID 1780880Notes

Reaction equation

HRID 1780880 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH:6]1[C:15]2[CH:14]=[C:13]3C=CC=C[C:12]3=[CH:11][N+:10]=2[CH:9]=[CH:8][CH:7]=1.C1(C(C2C=CC=CC=2)=C)C=CC=CC=1.O>[N+](C)([O-])=O>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH:6]1[C:15]2[N+:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 107401,1-DiphenylethyleneHCID 15186200Pyrido[1,2-b]isoquinolin-5-ium perchlorate

Product 1

HCID 22748827HCID 22748827, compound

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A mixture of 4.6 g (0.0165 mol) of benzo[b]quinolizinium perchlorate and 9 g of 1,1-diphenylethylene (0.05 mol) in 250 mL of nitromethane was heated to reflux under nitrogen for 16 h. The reaction mixture was poured into 100 mL of water, shaken, and the organic layer was separated and washed with 100 mL of water, and the nitromethane layer was concentrated in vacuo to 50 mL of its volume. To the above nitromethane layer was added 100 mL of water, the resulting mixture was concentrated in vacuo, and the residue was dissolved in 200 mL of acetonitrile and 500 mL of water. The above mixture was extracted with hexane (3×100 mL; a black oil insoluble in both hexane and acetonitrile/water was removed), and the aqueous layer was steam distilled to remove acetonitrile to yield an oil which crystallized on standing. The solid product was washed with 200 mL of ether, 200 mL of hexane, and 200 mL of ether to afford 5.1 g (67%) of 6,11-ethano-12,12-diphenyl-6,11-dihydrobenzoro]quinolizinium perchlorate, as a tan solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 16 h
  3. customthe organic layer was separated
  4. washwashed with 100 mL of water
  5. concentrationthe nitromethane layer was concentrated in vacuo to 50 mL of its volume
  6. additionTo the above nitromethane layer was added 100 mL of water
  7. concentrationthe resulting mixture was concentrated in vacuo
  8. dissolutionthe residue was dissolved in 200 mL of acetonitrile
  9. extractionThe above mixture was extracted with hexane (3×100 mL
  10. customa black oil insoluble in both hexane and acetonitrile/water was removed), and the aqueous layer
  11. distillationdistilled
  12. customto remove acetonitrile
  13. customto yield an oil which
  14. customcrystallized
  15. washThe solid product was washed with 200 mL of ether, 200 mL of hexane, and 200 mL of ether

Sources & evidence

ORD record
ord-4dd5f45edfe740e48aee6b1038b9860d
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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