Sodium Iodide → N-(3-{1-[(3R)-3-(3,4-Dimethoxyphenoxy)-3-Phenylpropyl]-4-Piperidinyl}Phenyl)-2-Methylpropanamide

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium carbonate (321 mg, 2.32 mmol), sodium iodide (522 mg, 3.48 mmol), 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide (570 mg, 2.32 mmol) and 4-{[(1R)-3-chloro-1-phenylpropyl]oxy)-1,2-dimethoxybenzene (712 mg, 2.32 mmol) in DMF (5.00 mL) was stirred at 100° C. for 3 h, at which time TLC indicated that the reaction was complete. The reaction mixture was poured into water (50 mL) and the aqueous layer was extracted with methylene chloride (3×30 mL). The combined organic extracts were washed with brine (30 mL), dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by Preparatory TLC [2.5% of NH3 (2.0 M in methanol) in CHCl3] to afford the product (970 mg, 90.1%) as a thick oil.

Provenance & Evidence