Water → HCID 22748827, compound

Participants

Reaction Steps

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.

Provenance & Evidence