N-Methylpiperidine → 24192-95-8

Participants

Reaction Steps

These intermediates were prepared following a procedure by K. Yoshida et al, J. Chem. Soc. Perkins Transactions I., (1992), 919-922. A solution of 2,4-dichloropyrimidine (4.00 g, 26.8 mmol) and 1-methyl-piperidine (3.25 mL, 29.5 mmol) in 1,4-dioxane (60 mL) was stirred at 100° C. for 3 d, then cooled and evaporated. Purification by flash chromatography (SiO2) eluted with 15:85 ethyl acetate: hexanes provided 4-chloro-2-piperidin-1-yl-pyrimidine (0.58 g, 12% yield) as a pale yellow solid: 1H-NMR (CDCl3, 500 MHz) 8.06 (d, 1H), 6.37 (d, 1H), 3.70 (m, 4H), 1.61 (m, 2H), 1.53 (m, 4H) ppm; MS (FIA) 198.1 (M+H); HPLC (method A) 3.550 min. and 2-chloro-4-piperidin-1-yl-pyrimidine (1.87 g, 38% yield) as a white solid: 1H-NMR (CDCl3, 500 MHz) 8.01 (d, 1H), 6.41 (d, 1H), 3.65 (m, 4H), 1.73 (m, 2H), 1.65 (m, 4H) ppm; MS (FIA) 198 (M+H); HPLC (method A) 2.583 min.

Provenance & Evidence