Potassium Carbonate → Methyl 2-[4-benzylpiperazinyl]benzoate

HRID 228073

Reaktionsgleichung

F[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:12]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.O>[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH2:21][CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

To a 250 mL pressure bottle equipped with magnetic stirring was added methyl 2-fluorobenzoate (Lancaster Synthesis Inc.) (3.0 g, 20 mmol), 1-benzylpiperazine (Aldrich) (3.8 g, 22 mmol) and K2CO3 (3.0 g, 22 mmol) in DMF (100 mL). The mixture was heated at 150° C. for 12 h. After cooling to RT the reaction was diluted with EtOAc (100 mL) and H2O was added. The organic layer was separated and washed with H2O, brine, dried over Na2SO4, filtered and concentrated in vacuo to afford a brown oil. The crude material was purified by column chromatography (4:1 hexanes-EtOAc) to give the title compound as a white foam (3.6 g). MS (ESI, pos. ion) m/z: 311 (M+H). Calc'd for C19H22N2O2: 310.17.

Aufarbeitung

customTo a 250 mL pressure bottle equipped
temperatureAfter cooling to RT the reaction
additionwas added
customThe organic layer was separated
washwashed with H2O, brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customto afford a brown oil
customThe crude material was purified by column chromatography (4:1 hexanes-EtOAc)

Quellen und Nachweise

ORD-Eintrag: ord-e8696c8d17eb438c9f752089da2f8e11
Quelldatensatz: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07560460B2

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