Toluene → HCID 24883075, compound

Participants

Reaction Steps

To a solution of cis-(+/−)-1-(1,4′-bipiperidin-4-yl)octahydro-2H-benzimidazol-2-one hydrochloride salt from step B (70 mg, 0.18 mmol) in 5 ml acetone was added potassium carbonate (49 mg, 0.36 mmol) followed by 1M isopropyl chloroformate in toluene (0.36 mL, 0.36 mmol) and the mixture was stirred at room temperature for 3 h. Removal of solvent gave a residue, which was dissolved in dichloromethane, and then water was added. The mixture was passed through VARIAN CHEM ELUT™ cartridges. The cartridge was rinsed with dichloromethane (2×20 mL). The dichloromethane solution was concentrated in vacuo and the crude product was purified by high pH prep-LCMS H to afford the title compound (40 mg, 56%). 1H NMR (400 MHz, CDCl3): δ ppm 1.14-1.21 (m, 1H), 1.23 (d, J=6.25 Hz, 6H), 1.33-1.48 (m, 3H), 1.48-1.67 (m, 6H), 1.66-1.95 (m, 8H), 2.43 (t, J=10.94 Hz, 1H), 2.71 (t, J=12.21 Hz, 2H), 2.95 (dd, J=21.09, 10.35 Hz, 2H), 3.52-3.63 (m, 2H), 3.68 (t, J=12.01 Hz, 1H), 4.02 (s, 1H), 4.20 (s, 2H), 4.80-4.98 (m, 1H). MS (M+1): 393.3

Provenance & Evidence