Ammonium Chloride → 1-Methyl-1-phenyl-2-benzyl-1,2,3,4-tetrahydroisoquinoline

Participants

Reaction Steps

To a suspension of 1-phenyl-2-benzyl-3,4-dihydroisoquinolinium iodide (1.0 g) in diethyl ether (10 ml) was added 3 M diethyl ether solution of methylmagnesium bromide (4.5 ml). The mixture was refluxed for 30 minutes with stirring and then poured into saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The separated organic layer was washed with water, sodium chloride aqueous solution and dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from n-hexane to give 1-methyl-1-phenyl-2-benzyl-1,2,3,4-tetrahydroisoquinoline (0.64 g).

Provenance & Evidence