Cesium carbonate → 1-[4-(4-Methoxy-3-nitro-phenyl)-piperazin-1-yl]ethanone

HRID 1366282Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([O:8][CH3:9])[CH:7]=1.[C:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)(=[O:15])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:9][O:8][C:6]1[CH:7]=[CH:2][C:3]([N:19]2[CH2:20][CH2:21][N:16]([C:13](=[O:15])[CH3:14])[CH2:17][CH2:18]2)=[CH:4][C:5]=1[N+:10]([O-:12])=[O:11]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-bromo-1-methoxy-2-nitrobenzene (300 mg, 1.29 mmol) in dioxane, 1-acetyl piperazine (400 mg, 3.12 mmol), cesium carbonate (1.0 g, 3.07 mmol), palladium diacetate (29.0 mg, 0.129 mmol) and 2-(di-t-butylphosphino)biphenyl (77 mg, 0.258 mmol) are added and stirred at 100° C. for 8 hours. After cooling, the mixture is filtered to remove insoluble material. The filtrate is poured into water and extracted with ethyl acetate twice. The organic layer is washed with water and then brine, dried over magnesium sulfate, and evaporated in vacuo. The residue is purified by silica gel column chromatography (n-hexane:ethyl acetate gradient) to afford 1-[4-(4-Methoxy-3-nitro-phenyl)-piperazin-1-yl]-ethanone (319 mg, 44%) as yellow solids.

Workup

temperatureAfter cooling
filtrationthe mixture is filtered
customto remove insoluble material
additionThe filtrate is poured into water
extractionextracted with ethyl acetate twice
washThe organic layer is washed with water
dry with materialbrine, dried over magnesium sulfate
customevaporated in vacuo
customThe residue is purified by silica gel column chromatography (n-hexane:ethyl acetate gradient)

Sources & evidence

ORD record: ord-53ea4352878541ba8229858bf8c4fd1e
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893074B2

Reaction notes

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