2,2,6,6-Tetramethylpiperidine → HCID 69935615, compound

Participants

Reaction Conditions

Reaction Steps

The compound 3,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (250 mg, 1.1 mmol) was dissolved in dry DMF (1 mL) taken in a shield tube. To the reaction mixture was added 6-bromonicotinonitrile (210 mg, 1.1 mmol) followed by 2,2,6,6-tetramethyl piperidine (0.16 g, 1.1 mmol) and the mixture was heated to 150° C. for 5 h. Reaction mixture was cooled to room temperature. The product was extracted with EtOAc and the organic layer was washed with H2O and brine. Solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 20-25% EtOAc in petroleum ether) to afford tert-butyl 4-(5-cyanopyridin-2-yl)-3,5-dimethylpiperazine-1-carboxylate (0.12 g, yield 33%). 1H NMR (400 MHz, CDCl3) δ 8.45 (d, J=2.3 Hz, 1H), 7.64 (dd, J=9.0 Hz, J=2.3 Hz, 1H), 6.53 (d, J=9.0 Hz, 1H), 4.48 (m, 2H), 4.13-4.00 (m, 2H), 3.16-3.06 (m, 2H), 1.51 (s, 9H), 1.27 (s, 3H), 1.25 (s, 3H).

Provenance & Evidence