Reaktion #476936

Reaktionsgleichung

4-Nitrobenzoic acid

tert-butyl 1-piperazinecarboxylate

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

N-methylmorpholine

→

tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate

Ausbeute 94.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe reaction was then washed with saturated sodium bicarbonate solution and brine
2. 2
   TrocknenThe organic phase was dried over MgSO4
3. 3
   Sonstigethe solvent removed in vacuo
4. 4
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

4-Nitrobenzoic acid (1.00 g, 6.00 mmol), tert-butyl 1-piperazinecarboxylate (1.10 g, 6.00 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.70 g, 9.00 mmol) and N-methylmorpholine (1.30 ml, 12.00 mmol) were dissolved in dichloromethane (10 ml) and the reaction mixture stirred at 20° C. for 5 h. The reaction was then washed with saturated sodium bicarbonate solution and brine. The organic phase was dried over MgSO4 and the solvent removed in vacuo. The residue was purified by silica gel column chromatography using a 0-50% EtOAc in hexane gradient to afford tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate (1.88 g, 5.60 mmol, 94%) as a white solid. LCMS (1) Rt: 2.01 min; m/z (ES+) No M+H+, but 280 (-tBu) and 236 (-Boc).

Quelle