N,N-Dimethylpiperidin-4-amine → HCID 49783679, compound

Participants

Reaction Steps

To a solution of compound 26 (0.200 g, 0.59 mmol) in DCM was added TEA (0.090 g, 0.89 mmol) and 4-dimethylaminopiperidine (0.114 g, 0.89 mmol). The reaction was monitored by HPLC. The reaction was complete after stirring at room temperature for 16 hrs. DCM was removed in vacuo, and the resulting solid was dissolved in a minimal amount of DCM and purified with chromatography with a gradient of 10 to 30% MeOH in DCM. Pure fractions were combined and evaporated in vacuo to yield an oil, which was triturated with DCM and hexanes, and then filtered to yield compound 72 as a peach solid (0.124 g, 49% yield). HPLC purity: 96.5%; 1H NMR (500 MHz, DMSO-d6): δ 8.22 (d, J=2 Hz, 1H), 7.84 (dd, J1=2 Hz, J2=8 Hz, 1H), 7.41 (d, J=6 Hz, 1H), 7.39 (s, 1H), 7.34 (d, J=8 Hz, 1H), 6.70 (d, J=8 Hz, 1H), 3.8 (d, J=13 Hz, 2H), 2.84 (t, J=12 Hz, 2H), 2.31 (s, 3H), 2.26 (m, 1H), 2.25 (s, 3H), 2.15 (s, 6H), 1.79 (d, J=12 Hz, 2H), 1.43 (m, 2H); MS (ESI, EI+): m/z=430 (MH+); melting point: 136-139° C.

Provenance & Evidence