Triethylamine → 3-(2,2-Difluoro-benzo[1,3]dioxol-5-ylmethyl)-piperidine-1-carboxylic acid pyridin-3-ylamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]-piperidine hydrochloride (100 mg, 0.34 mmol) in CH3CN (2 mL) was added Et3N (0.07 mL, 0.52 mmol). To this reaction mixture, pyridin-3-yl-carbamic acid phenyl ester (77.0 mg, 1.05 mmol) was added and the reaction mixture was heated overnight at 35° C. The reaction mixture was then concentrated and the crude residue was purified (FCC, 2 N NH3 in MeOH/DCM) to give 3-(2,2-difluoro-benzo[1,3]dioxol-5-ylmethyl)-piperidine-1-carboxylic acid pyridin-3-ylamide (120 mg, 93%). MS (ESI+): calcd for C19H19F2N3O3 m/z 375.14, found 376.2 (M+H)+. 1H NMR (d4-methanol): 8.54 (d, J=2.3, 1H), 8.17-8.13 (m, 1H), 7.86 (ddd, J=8.4, 2.6, 1.4, 1H), 7.34-7.30 (m, 1H), 7.10-7.06 (m, 2H), 6.99 (dd, J=8.2, 1.5, 1H), 4.05-3.95 (m, 2H), 3.04-2.98 (m, 1H), 2.74-2.64 (m, 2H), 2.58-2.53 (m, 1H), 1.86-1.74 (m, 3H), 1.56-1.47 (m, 1H), 1.30-1.22 (m, 1H).

Provenance & Evidence