Trifluoroacetic acid → 4-(4-Nitrophenoxy)piperidine

Participants

Reaction Steps

A solution of 4-(4-nitro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (10.0 g, 31.02 mmol) in DCM (50 mL) was treated with TFA (50 mL) and stirred at ambient temperature for 2 hours. The solvent was removed under vacuum, the residue basified with NH4OH and extracted into DCM (3×). The combined extracts were washed with brine, dried over Na2SO4 and concentrated under vacuum to afford the title compound (7.81 g, quantitative yield) as a yellow residue. 1H NMR (300 MHz, CDCl3) δ 8.18 (m, 2H), 6.94 (m, 2H), 4.52 (m, 1H), 3.18 (m, 2H), 2.79 (m, 2H), 2.38 (br s, 1H), 2.05 (m, 2H), 1.72 (m, 2H). LCMS (m/z, Method A) ES+ 223.1 [M+1]+.

Provenance & Evidence