Potassium Carbonate → 4-[4-[(3-Benzyl-3-azabicyclo[3.2.1]oct-8-yl)(methyl)amino]-1-(3,4 dimethoxyphenoxy)butyl]benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-benzyl-N-methyl-3-azabicyclo[3.2.1]octan-8-amine (Preparation B; 1.3 g, 5.95 mmol), 4-(4-cyanophenyl)-4-(3,4-dimethoxyphenoxy)butyl methanesulfonate (Preparation I(iii); 2.41 g, 5.95 mmol), and potassium carbonate (822 mg, 5.95 mmol) in DMF (25 mL) was heated at 90° C. under nitrogen overnight. The mixture was partitioned with water (50 mL) and diethyl ether (40 mL). The aqueous layer was extracted with diethyl ether (2×40 mL). The combined organic extracts were washed with brine (2×30 mL), dried (Na2SO4), filtered and then concentrated in vacuo. The residue was chromatographed on silica gel, eluting with dichloromethane:methanol (98:2), to afford 860 mg (27%) of the sub-title compound.

Provenance & Evidence