Aluminum(III) Chloride → HCID 86755330, compound

Participants

Reaction Steps

To a suspension of 88.0 g (0.66 mol) of aluminium trichloride in 420 mL of absolute dichloromethane is added dropwise, at 0-5° C., a solution of 60.1 g (0.22 mol) of N-formyl-2-(2'-methoxyphenyl) methyl-3,3-dimethyl-4-methylene-piperidine (4) in 200 mL of dichloromethane within 2 h. The mixture is left to react for a further 3 h at 5° C. and then poured onto 800 mL of ice. The organic phase is separated off and the aqueous phase is extracted twice more with 250 mL of dichloromethane. The combined organic phases are dried over MgSO4 and the solvent is eliminated in vacuo. The residue is chromatographed on silica gel (500 g silica gel, solvent: ethyl acetate). 36.0 g (60%) of trans-1-formyl-8-methoxy-3a, 4,4-trimethyl-2,3,3a,4,9,9a-hexahydro-1H-benz[f]indole (5) are obtained as an oil.

Provenance & Evidence