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 bromide (353.1 g) in tetrahydrofuran (3.5 l) was added 2.0M tetrahydrofuran solution of methylmagnesium bromide (700 ml) for 1.5 hours with stirring at room temperature. After additional stirring for 1.5 hours, the mixture was poured into a solution of ammonium chloride (300 g) in water (650 ml) under ice cooling. After separation, the aqueous layer was extracted with ethyl acetate (3.5 l). The combined organic layers were washed with water (1 l), sodium chloride aqueous solution (1 l) and dried over magnesium sulfate (125 g) and evaporated in vacuo. The residue was crystallized from ethanol (500 ml) to give 1-methyl-1-phenyl-2-benzyl-1,2,3,4-tetrahydroisoquinoline (254.0 g).

Provenance & Evidence