Hydrochloric Acid → 1-Benzyl-3-[3-(1-Naphthylsulfonylmethyl)-4-nitrophenoxy]-piperidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-benzyl-3-(4-nitrophenoxy)piperidine (1.0 g, 3.14 mmoles) and 1-chloromethanesulfonylnaphthalene (0.9 g, 3.8 mmoles) in THF at −78° C. was treated dropwise with a solution of 1M potassium t-butoxide (9 mL, 9 mmoles) over a 30 minute period, warmed to −40° C., stirred at −40° C. for 5 hours, poured into cold 2N HCl and extracted with EtOAc. The extracts were combined, dried over Na2SO4 and concentrated under vacuum. The resultant residue was purified by normal phase HPLC on a silica column, using as eluent 40% EtOAc/hexane, to afford the title compound as an off-white solid (1.2 g, 2.3 mmoles).

Provenance & Evidence