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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 478631Generated: October 26, 2026

Nitrogen → 4-(4-Benzyl-piperazin-1-YL)-benzoic acid methyl ester

https://huagongshe.com/reaction/478631

Reaction equation

Participants

RoleNameHCIDCharge
ReactantNitrogenHCID 947—
ReactantOxygenHCID 977—
ReactantMethyl 4-bromobenzoateHCID 12081—
Reactant1-BenzylpiperazineHCID 75994—
Reactant2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 2734217—
ReactantSodium t-butoxideHCID 23676156—
SolventTolueneHCID 1140—
SolventDiethyl EtherHCID 3283—
SolventEthyl AcetateHCID 8857—
Product4-(4-Benzyl-piperazin-1-YL)-benzoic acid methyl esterHCID 53406803—

Reaction Steps

Tris-(dibenzylidene-acetone)-dipalladium (0.03 mmol), (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (0.9 mmol) and NaOtBu (6.5 mmol) are suspended in toluene (20 ml) in an oxygen-free atmosphere (N2). 4-Bromo-benzoic acid methyl ester (4.65 mmol) and 1-(benzyl)-piperazine (5.6 mmol) are added and the stirred mixture is heated under reflux for 4 hours. After cooling, a mixture of ethylacetate and diethylether is added and the mixture is filtered. Then the solvent is evaporated and the residue is suspended in diethylether and the solid filtered of and dried (vacuum). A pale powder with mp. 105-107° C., Rf=0.67 (CH2Cl2/MeOH=95:5) is obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06642239B2
Source datasetuspto-grants-2003_11
ORD IDord-8666121ee238419cbc06720dd0372e67
Source noteuspto-grants-2003_11