4-Nitrobenzyl chloroformate → HCID 18620712, compound

Participants

Reaction Steps

A mixture of (1-acetyl-4-piperidinyl)butyric acid (11.6 g, 54.4 mmol) and concentrated hydrochloric acid (30 ml) was refluxed for 16 hours, at the end of which time the hydrochloric acid was distilled off under reduced pressure. The residue was washed with ether and dissolved in 5N-NaOH/H2O (30 ml), followed by addition of ether (30 ml). To this mixture with ice-bath cooling was added p-nitrobenzyl chlorocarbonate (11.7 g, 54.3 mmol) in small portions, and the mixture was stirred at room temperature for 1 hour. This reaction mixture was acidified with 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated NaCl/H2O and dried over MgSO4, and the solvent was distilled off under reduced pressure. The residual oil was treated with ether to provide the title compound (13.5 g) as colorless powders.

Provenance & Evidence