p-Fluoronitrobenzene → Tert-butyl 4-(4-nitrophenoxy)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

1-Fluoro-4-nitrobenzene (10.0 g, 70.9 mmol) was melted into 4-hydroxy-1-Boc-piperidine (12.97 g, 64.4 mmol). The mixture obtained was treated with a 25 wt % potassium hydroxide solution (60 mL) and tetrabutylammonium bromide (1.60 g, 4.96 mmol) and heated at 40° C. for 70 hours. The precipitate was collected by filtration, washed with water and air-dried to leave the title compound (22.7 g, quantitative yield) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.20 (m, 2H), 6.95 (m, 2H), 4.60 (m, 1H), 3.70 (m, 2H), 3.38 (m, 2H), 1.97 (m, 2H), 1.78 (m, 2H), 1.48 (s, 9H).

Provenance & Evidence