Diisopropylethylamine → 4-chloro-N-(1-methylpiperidin-4-yl)picolinamide

Participants

Reaction Steps

A 0° C. solution of 1-methyl-4-amino-piperidine (0.860 g, 7.53 mmol) and DIEA (2.63 mL, 15.06 mmol) in THF (15 mL) was treated with 4-chloropicolinoyl chloride hydrochloride (0.8 g, 3.77 mmol) in one portion, stirred at RT for 2 h, diluted with EtOAc and washed with satd. NaHCO3, then brine. The organic layer was dried over Na2SO4 and concentrated to dryness to afford 4-chloro-N-(1-methylpiperidin-4-yl)picolinamide (1.07 g, 112%). 1H NMR (400 MHz, DMSO-d6): δ 8.61-8.60 (m, 2H), 8.00 (d, J=2.1 Hz, 1H), 7.75 (dd, J=5.3, 2.2 Hz, 1H), 3.74-3.72 (m, 1H), 2.71 (d, J=11.3 Hz, 2H), 2.13 (s, 3H), 1.93 (m, 2H), 1.69-1.67 (m, 4H); MS (ESI) m/z: 254.1 (M+H+).

Provenance & Evidence