N,N-Dimethylpiperidin-4-amine → 1-(5-bromopyridin-2-yl)-N,N-dimethylpiperidin-4-amine

Participants

Reaction Conditions

Reaction Steps

Mix 5-bromo-2-fluoro-pyridine (1.00 g, 5.68 mmol) and N,N-dimethyl-piperidin-4-yl-amine (1.50 g, 11.70 mmol) together and heat to 80° C. for 64 h. Partition the reaction between CH2Cl2 (5 mL) and 1N NaOH (8 mL). Collect the organic phase and extract the aqueous phase with additional CH2Cl2 (2×20 mL). Combine the organic solutions, then dry, filter, and concentrate. Purify the crude material by flash chromatography using an eluent of 5% MeOH (2N NH3)/CH2Cl2 to give 1.49 g (92%) of the title compound as a white solid. 1H NMR (CDCl3) δ 1.46 (dq, 2H, J=4.0, 11.8 Hz), 1.86 (br d, 2H, J=12.8 Hz), 2.26 (s, 6H), 2.32 (m, 1H), 2.80 (dt, 2H, J=2.7, 12.8 Hz), 4.23 (br d, 2H, J=13.2 Hz), 6.53 (d, 1H, J=8.9 Hz), 7.46 (dd, 1H, J=2.8, 9.0 Hz), 8.13 (d, 1H, J=2.6 Hz).

Provenance & Evidence