4-Nitrobenzoic Acid → Tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate

HRID 714986Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:13]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:16]2[CH2:15][CH2:14][N:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:18][CH2:17]2)=[O:10])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 20 °C

Procedure

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).

Workup

washThe reaction was then washed with saturated sodium bicarbonate solution and brine
dry with materialThe organic phase was dried over MgSO4
customthe solvent removed in vacuo
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-53e1a21ba32f49cdb7c7ba9f06732cf0
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187465B2

Reaction notes

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