Aniline → 1-Boc-4-AP

Participants

Reaction Steps

1.53 g (7.68 mmol) of BOC-piperidone and 13.4 g (77 mmol) of sodium sulfate in 28 mL acetic acid were treated with 0.78 mL (8.6 mmol) of aniline. After 10 min, 8.2 g (39 mmol) of sodium triacetoxyborohydride was added. After 45 min, the solution was poured onto ice, and neutralized by portionwise addition of solid sodium bicarbonate (ca. 45 g). The resulting solution was extracted with five portions of CHCl3 ; the organics were washed with brine, dried over MgSO4, filtered, concentrated, and purified via flash chromatography (10:1 to 5:1 to 2:1 hexane-EtOAc) to provide 1.703 g of the title compound as a white solid.

Provenance & Evidence