Acetic Acid → tert-Butyl 4-(2-chloroanilino)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of N-(tert-butoxycarbonyl)-4-piperidone (8.01 g, 39.4 mmol), 2-chloroaniline (5.74 g, 44.1 mmol) and acetic acid (2.80 g, 46.6 mmol) in 200 ml ethylene chloride ethane was added sodium triacetoxyborohydride (8.37 g, 78.8 mmol). The mixture was stirred at room temp for 2.5 days. Added 2N NaOH solution to adjust pH to 10. The organic phase was separated and washed with water, then dried over Na2SO4. Solvent was removed under vacuum and crude product was purified with flash column chromatography to yield tert-butyl-4-(2-chlorophenylamino)piperidine-1-carboxylate in 8.2% yield (1.6 g) as white solid.

Provenance & Evidence