Benzo[b]quinolizinium hexafluorophosphate → Dihydrobenzo[b]quinolizinium hexafluorophosphate

Participants

Reaction Steps

A mixture of 6 g (0.0196 mol) of benzo[b]quinolizinium hexafluorophosphate and 5.12 g (0.023 mol) of 4-(3-furyl)-6,7-dihydrothianaphthene in 100 mL of nitromethane was heated to reflux for 14 h, cooled, and concentrated in vacuo. The residue was dissolved in ethyl acetate (200 mL), filtered, and the filtrate was concentrated in vacuo, the residue was dissolved in ether, and the ether solution was cooled to yield 11 g of 6,11[5',']-4'-(3-furyl)-4',5',6',7'-tetrahydrothianaphthyl]6,11-dihydrobenzo[b]quinolizinium hexafluorophosphate as a gray solid, (1:1.03 mixture of isomers). The gray solid, product was dissolved in 500 mL of isopropanol/methylene chloride (3:2) on a steam-bath while distilling 150 mL of methylene chloride and cooled to afford 6,11[[5',4']-4'-(3-furyl)-4',5',6',7'-tetrahydrothianaphthyl]6,11]-dihydrobenzo[b]quinolizinium hexafluorophosphate, (Formula I: R1 =R2 =R3 =R7 =H; ##STR56## R5 =3-furyl; X- =PF6- ; and Formula I: R1 =R2 =R4 =R7 =H; ##STR57## R6 =3-furyl; X-=PF6-), as a tan solid (1:1 mixture of isomers).

Provenance & Evidence