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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1503830Generated: October 31, 2026

Cesium carbonate → tert-Butyl 4-(2-methyl-4-nitrophenyl)piperazine-1-carboxylate

https://huagongshe.com/reaction/1503830

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactanttert-Butyl piperazine-1-carboxylateHCID 143452—
Reactant1-Bromo-2-methyl-4-nitrobenzeneHCID 251672—
Reactant2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11155794—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Solvent1,4-DioxaneHCID 31275—
Producttert-Butyl 4-(2-methyl-4-nitrophenyl)piperazine-1-carboxylateHCID 22336105—

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of 1-bromo-2-methyl-4-nitrobenzene (5.16 g, 24 mmol), tert-butyl piperazine-1-carboxylate (4.46 g, 24 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (1.15 g, 2.4 mmol), cesium carbonate (15.65 g, 48 mmol) and tris(dibenzylideneacetone)dipalladium (2.21 g, 2.4 mmol) in 1,4-dioxane (120 mL) was heated at 100° C. for 16 hours. The solid was filtered and the filtrate was concentrated to give the crude product which was purified by flash chromatography on silica gel (200-300 mesh) eluting with 20/1 petroleum ether/ethyl acetate to give the title compound. MS: 322 (M+H+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09212192B2
Source datasetuspto-grants-2015_12
ORD IDord-6d0f4bdc551f464493a90f0dbfa990a3
Source noteuspto-grants-2015_12