4-Nitrophenol → HCID 12094715, compound

Participants

Reaction Steps

A chilled solution of 4-nitrophenol (1.14 g, 8.12 mmol), triphenyl phosphine (3.21, 12.2 mmol) and 1-benzyl-4-hydroxypiperidine (2.6 g, 14 mmol) in THF was treated with diisopropyl azodicarboxylate (DIAD) (2.4 mL, 12 mmol), stirred at ambient temperatures, under nitrogen, for 17.5 hours, poured into excess water and extracted with ethyl acetate. The extracts were combined, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash chromatography with 30-40% ethyl acetate in hexane to give 1-benzyl-4-(4-nitro-phenoxy)-piperidine as a yellow semi-solid, 0.880 g (35% yield); Mass spectrum (+EI, [M+H]+) m/z 313. 1HNMR (500 MHz, DMSO-d6): δ8.11-8.15 (m, 2H), 7.24-7.30 (m, 4H), 7.18-7.22 (m, 1H), 7.10-7.14 (m, 2H), 4.53-4.59 (m, 1H), 3.45 (s, 2H), 2.60-2.64 (m, 2H), 2.20-2.26 (m, 2H), 1.91-1.95 (m, 2H), 1.58-1.67 ppm (m, 2H).

Provenance & Evidence