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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 317Generated: October 25, 2026

Piperazine → 4-Chloro-2-(piperazin-1-yl)benzonitrile

https://huagongshe.com/reaction/317

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPiperazineHCID 4837—
Reactant2-Bromo-4-chlorobenzonitrileHCID 23498524—
ReagentCesium carbonateHCID 10796—
CatalystBinap, (A+-)-HCID 634876—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Solvent1,4-DioxaneHCID 31275—
Product4-Chloro-2-(piperazin-1-yl)benzonitrileHCID 179292380%

Reaction Conditions

Temperature90 °C

Reaction Steps

Tris(dibenzylideneacetone)dipalladium (0) (43.4 mg, 0.05 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (59.0 mg, 0.09 mmol) were added to a mixture of 2-bromo-4-chlorobenzonitrile (205 mg, 0.95 mmol), Cesium carbonate (463 mg, 1.42 mmol) and Piperazine (163 mg, 1.89 mmol) in dioxane (3 mL). Reaction vessel was placed in an oil bath set to 90 °C 2.45pm. LCMS o/n shows large product peak (222). Cooled, filtered through a silica plug, washing with EtOAc until filtrate is clear. Crude NMR is very messy, target deprioritized. Discarded.

Provenance & Evidence

Source dataset750 AstraZeneca ELN dataset
ORD IDord-124e8e40d3e54042af531dbb1d8d85d1
Source note750 AstraZeneca ELN dataset