4-Chloropyridine → 4-(Diallylamino)pyridine

Participants

Reaction Steps

4-Diallylaminopyridine was prepared by the condensation of 4-chloropyridine with diallylamine, as described by Mathias and Cei (Macromolecules, 1987, 20, 2645). This product was hydrosilylated with diethoxymethylsilane in the presence of chloroplatinic acid, as described by Rubinsztajn, et al, (Macromolecules, 1990, 23, 4026) to yield 4-bis(3'-diethoxymethylsilylpropyl)aminopyridine. Finally, following a procedure similar to that described by Tundo and Venturello (J. Amer. Chem. Soc., 1979, 101, 6606), this product was heated with activated silica (Davison Grade 22, 60-200 mesh, 60 Angstrom, 500 m2 /gram BET surface area, 0.75 cm3 /gram pore volume), to give the silica bound dialkylaminopyridine with the loss of ethanol. After drying in a vacuum oven at 45° C. for 18 hours, this material found to contain 0.6 meq aminopyridine/gram.

Provenance & Evidence