4-Pyridineacetic acid hydrochloride → 4-Piperidineacetic acid

Participants

Reaction Steps

Pyridin-4-yl-acetic acid hydrochloride (20.0 g, 115 mmol) was added to water/25% ammonia (125 mL:10 mL). The mixture was degassed and flushed with nitrogen before addition of rhodium on activated alumina (0.45 g). The mixture was again degassed, then stirred in a hydrogen atmosphere at 50 bar for 16 h. Filtration of the reaction mixture through filter paper afforded the bulk of the catalyst which was recycled after washing with methanol. The filtrate was then filtered through Celite and concentrated to afford a white solid (19.7 g, 96% yield).

Provenance & Evidence