Acetic Acid → 1-Benzyl-piperidin-4-yl 2-amino-4-bromo-benzoate

Participants

Reaction Steps

0.42 g (0.001 mol) of 1-benzyl-piperidin-4-yl 4-bromo-2-nitro-benzoate was dissolved in 6 ml of ethanol and treated with 6 ml of glacial acetic acid and 0.225 g (0.004 mol) of iron powder. The mixture was boiled at reflux for 6 hrs. and concentrated and the residue was made basic with sat. sodium carbonate solution. The aqueous phase was extracted with ethyl acetate and the organic phase was washed with sat. sodium chloride solution and dried over sodium sulfate. After concentration the residue was chromatographed on silica gel with ethyl acetate/hexane (1:4). 0.415 g (100%) of 1-benzyl-piperidin-4-yl 2-amino-4-bromo-benzoate was obtained as white crystals.

Provenance & Evidence