The condensation of anthranilonitrile (I) with cyclohexane-1,3-dione (II) in the presence of p-toluenesulfonic acid (removal of water) gives the enaminoketone (III). Cyclization of (III) in the presence of K2CO3 and CuCl yields the aminoketone (IV), which is then reduced with LiAlH4.
The condensation of N-(2-methylquinolin-4-yl)acetamide (I) with 2-(2-iodoethyl)-1,3-dioxane (II) by means of LDA in THF gives the corresponding adduct (III), which is then cyclized and deacylated by means of aqueous HCl to afford the target tetrahydroacridine.