4-Methylpiperidine → HCID 49783917, compound

Participants

Reaction Steps

Sulfonyl chloride 36 (0.20 g, 0.55 mmol) was combined with 4-methylpiperidine (0.16 g, 1.65 mmol) and TEA (0.17 g, 1.65 mmol) in DCM (5 mL). The solution was stirred overnight at room temperature. Upon consumption of starting material, as determined via TLC (75% EtOAc in hexanes), the reaction mixture was partitioned between DCM and water. After 3 extractions, the combined organic extracts were washed sequentially with saturated aqueous NaHCO3, water, and brine. The crude product was chromatographed on normal-phase silica to yield the desired product 87 (0.167 g, 71.4% yield, 97.1% pure). 1H NMR (500 MHz, DMSO-d6): δ 8.28 (d, J=2 Hz, 1H), 8.07 (dd, J1=9 Hz, J2=2 Hz, 1H), 7.72 (d, J=8 Hz, 1H), 7.46 (dd, J1=5 Hz, J2=2 Hz, 1H), 7.44 (d, J=2 Hz, 1H), 7.10 (d, J=9 Hz, 1H), 3.70 (d, J=12 Hz, 2H), 2.74 (ddd, J1=J2=12 Hz, J3=2 Hz, 2H), 1.65 (dd, J1=13 Hz, J2=2 Hz, 2H), 1.44 (m, 1H), 1.09 (ddd, J1=28 Hz, J2=13 Hz, J3=4 Hz, 2H), 0.87 (d, J=7 Hz, 3H); MS (ESI, EI+): m/z=425.11 (MH+); melting point: 127-130° C.

Provenance & Evidence