Water → 6-Bromo-8-piperazin-1-yl-quinoline

HRID 992062

Reaktionsgleichung

C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]([Br:24])[CH:17]=[C:18]3[C:23]=2[N:22]=[CH:21][CH:20]=[CH:19]3)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClCCOC(Cl)=O.ClC(OC=C)=O.O>ClC(Cl)C>[Br:24][C:16]1[CH:17]=[C:18]2[C:23](=[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH:15]=1)[N:22]=[CH:21][CH:20]=[CH:19]2

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 8-(4-benzyl-piperazin-1-yl)-6-bromo-quinoline (1.6 g, 4.2 mmol) in dichloroethane (50 mL) under a N2 atmosphere was added chloroethylchloroformate (1.26 mL, 12.6 mmol) and the reaction mixture was heated at 80° C. for 4 hours, and at ambient temperature overnight. No reaction was observed by TLC, therefore vinyl chloroformate (0.35 mL, 6.3 mmol) was added and the reaction was heated at 80° C. for another 4 hours. The cooled reaction was poured into H2O and extracted into CH2Cl2 (2×100 mL) and EtOAc (100 mL). The organic fractions were combined, dried over Na2SO4, and left in EtOAc overnight. The organic layer was concentrated and purified by column chromatography (10%MeOH/CH2Cl2+NH4OH) affording 1.03 g (84%) of a brown foam. MS (+) APCI m/z 292 [M+H]+.

Aufarbeitung

customat ambient temperature
customovernight
temperaturethe reaction was heated at 80° C. for another 4 hours
customThe cooled reaction
extractionextracted into CH2Cl2 (2×100 mL) and EtOAc (100 mL)
dry with materialdried over Na2SO4
concentrationThe organic layer was concentrated
custompurified by column chromatography (10%MeOH/CH2Cl2+NH4OH)

Quellen und Nachweise

ORD-Eintrag: ord-b652a761a23f4c48b74f87fc8133749b
Quelldatensatz: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06465482B2

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