4-Fluorobenzonitrile → 4-(p-Cyanophenoxy)-2-methyl-1,2,3,4-tetrahydroisoquinoline

Participants

Reaction Steps

A solution of 1,2,3,4-tetrahydro-2-methyl-4-isoquinolinol (3.0 g, 0.018 mole) in dry DMF (15 ml) is added dropwise under nitrogen to a suspension of sodium hydride 50% (98%) (1.1 g, 0.022 mole), previously washed with hexane, in dry DMF (25 ml). The mixture is warmed to 60° C., at which time a solution of 4-fluorobenzonitrile (2.2 g, 0.018 mole) in dry DMF (15 ml) is slowly added. The reaction mixture is stirred at room temperature for 16 hours.

Provenance & Evidence