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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 2182141Erstellt: 27. Oktober 2026

Piperazine → 2-[(3-Cyanobenzyl)Oxy]-6-(1-Piperazinyl)Pyrazine

https://huagongshe.com/reaction/2182141

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktPiperazineHCID 4837—
EduktBinap, (A+-)-HCID 634876—
Edukt3-(6-Chloro-pyrazin-2-yloxymethyl)-benzonitrileHCID 22481973—
EduktSodium t-butoxideHCID 23676156—
KatalysatorBis(dibenzylideneacetone)palladiumHCID 9811564—
LösungsmittelTolueneHCID 1140—
Produkt2-[(3-Cyanobenzyl)Oxy]-6-(1-Piperazinyl)PyrazineHCID 985733522,4%

Reaktionsbedingungen

Temperatur90 °C

Reaktionsschritte

A mixture of 3-(6-chloro-pyrazin-2-yloxymethyl)-benzonitrile I-3f (667.2 mg, 2.716 mmol), piperazine (297 mg, 3.531 mmol), sodium t-butoxide (287 mg, 2.987 mmol), BINAP (67.7 mg, 0.109 mmol), and Pd2(dba)3 (49.7 mg, 0.054 mmol) in toluene (10 mL) was heated at 90° C. overnight. The solution was cooled to room temperature and filtered through a celite pad. The celite pad was washed with ethyl acetate several times. The combined filtrate was concentrated in vacuo to give the crude title compound. The product was purified by chromatography (silica, 10% MeOH/dichlormethane with 1% NH4OH) to give 180 mg 3-(3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-6′-yloxymethyl)-benzonitrile (3-E).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS06894050B2
Quelldatensatzuspto-grants-2005_05
ORD IDord-e6a659b29715454186b3e8c2350cf27b
Quellennotizuspto-grants-2005_05