4-Aminomethyl chromans: dependence of serotonin and dopamine binding upon aromatic ring substitution

The synthesis of two series of methoxy-substituted 4-aminomethyl chromans is described. The formation of the pyran ring is achieved via an intramolecular Friedel-Crafts reaction of the appropriate epoxide. There is a profound dependence between the position of the aromatic methoxy substituent and the binding affinity for the 5-HT1A and dopamine D-2 receptors.