Potassium Carbonate → Tert-butyl 3-[3-(4-cyanoanilino)propyl]-3-azabicyclo[3.2.1]oct-8-yl-(methyl)carbamate

Participants

Reaction Steps

A mixture of tert-butyl 3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate (Preparation D; 2.90 g, 12.1 mmol), 3-(4-cyanoanilino)propyl 4-methyl-benzenesulfonate (see step (ii) above; 3.98 g, 12.1 mmol), and potassium carbonate (1.67 g, 12.1 mmol) in DMF (50 mL) was heated at 90° C. under nitrogen for 4 h. The mixture was partitioned with water (50 mL) and diethyl ether (50 mL). The aqueous layer was separated and then extracted with diethyl ether (2×50 mL). The combined organic extracts were washed with saturated 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 2.85 g (59%) of the sub-title compound.

Provenance & Evidence