Water → tert-Butyl 4-(3-aminophenyl)piperazine-1-carboxylate

HRID 1633593

Reaction equation

[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.F[C:15]1[CH:16]=[C:17]([N+:21]([O-])=O)[CH:18]=[CH:19][CH:20]=1.O>CN1C(=O)CCC1>[C:10]([O:9][C:7]([N:1]1[CH2:6][CH2:5][N:4]([C:15]2[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=2)[NH2:21])[CH2:3][CH2:2]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of tert-butyl 1-piperazinecarboxylate (4 g, 21.5 mmol) and 3-fluoronitrobenzene (2.3 ml, 21.5 mmol) in anhydrous NMP (5 ml) was heated to 120° C. for 3 days. After cooling water (25 ml) was added and the mixture was extracted with ethyl acetate (2×10 ml). The organic extract was dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by column-chromatography using successively petroleum ether and a mixture of ethyl acetate and petroleum ether (1:1 v/v) as the eluents. Yield of t-butyl 4-(3-nitrophenyl)-1-piperazinecarboxylate: 1.34 g (20%). This intermediate was quantitatively hydrogenated to 2g in ethanol at ambient pressure using Pd (5% on activated carbon) as the catalyst.

Workup

additionwas added
extractionthe mixture was extracted with ethyl acetate (2×10 ml)
extractionThe organic extract
dry with materialwas dried over sodium sulfate
customthe solvent was removed under reduced pressure
customThe residue was purified by column-chromatography
additiona mixture of ethyl acetate and petroleum ether (1:1 v/v) as the eluents

Sources & evidence

ORD record: ord-c4fbda0980894972b8318a8c05c224dc
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503925B1

Linked notes

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