Sodium Iodide → HCID 10186210, compound

Participants

Reaction Steps

A solution of 3-((αR)-α-((2S,5R)-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl)-N,N-diethylbenzamide (0.49 g, 1.20 mmol) in acetonitrile (10 mL) was added to sodium iodide (100 mg), sodium carbonate (0.70 g, 6.64 mmol) and stirred under nitrogen at room temperature during the addition of 3-fluorobenzyl bromide (0.16 mL, 1.32 mmol). The reaction was complete in 3 hours. The solvent was removed by evaporation and the residue was partitioned between methylene chloride and water. The aqueous layer was extracted with methylene chloride twice more, and the combined organic extracts were dried (Na2SO4/MgSO4) and concentrated under reduced pressure. The residual brown oil was purified by chromatography on silica gel (EtOAc/CH2Cl2) to give 0.37 g (0.71 mmol) of the desired product as a light brown amorphous solid. The salt was made by dissolving the amine in ethanol and titrating to pH 3.92 with 0.2 M HCl in ethanol. The salt was redissolved in water and lyophilized to obtain a light brown powdery solid. 1H NMR (300 MHz, CDCl3): δ 1.04–1.22 (m, 12H); 1.93–2.08 (m, 2H); 2.51–2.76 (m, 5H); 3.10–3.60 (m, 4H); 3.78 (s, 3H); 3.84–3.89 (d, J=13.3 Hz, 1H); 5.11 (s, 1H); 6.76–7.46 (m, 12H).

Provenance & Evidence