Thionyl Chloride → Tert-butyl 4-(cyano(phenyl)methylene)piperidine-1-carboxylate

Participants

Reaction Steps

To tert-butyl 4-[cyano(phenyl)methyl]-4-hydroxypiperidine-1-carboxylate (1.8 g, 5.69 mmol) in pyridine (4 ml) was added SOCl2 (2.076 ml, 28.4 mmol) and the reaction was stirred for 10 min. The reaction mixture was concentrated in vacuo. The resulting crystalline solid was adsorbed onto silica gel and purified by silica gel chromatography in an Isco Companion. The desired fractions were combined and concentrated in vacuo. 1.18 g, 70% over two steps.

Provenance & Evidence