Sodium Iodide → HCID 178430528, compound

Participants

Reaction Steps

To a solution of 3,4-dimethyl-4-(3-(1H-1,2,3-triazol-4-yl)phenyl)piperidine (Preparation 44, 50 mg, 0.20 mmol) in N,N-dimethylformamide (6 mL) was added commercially available 3-chloro-1-phenyl-1-propanol (33 mg, 0.21 mmol), sodium iodide (15 mg) and aqueous sodium hydrogencarbonate (25 mg, 0.29 mmol). The resultant mixture was heated to 80° C. and stirred overnight. The reaction mixture was cooled, poured onto saturated aqueous sodium hydrogencarbonate solution (100 mL) and extracted with ethyl acetate (3×20 mL). The combined extracts were dried over MgSO4, filtered and concentrated in vacuo to give an off-white gum. The crude product was purified by column chromatography on a 5 g silica Waters Sep-Pak3 eluting with dichloromethane and then dichloromethane:methanol (5:95) to give the title compound as a clear oil (19 mg, 25%).

Provenance & Evidence