Potassium Iodide → HCID 68515831, Verbindung

HRID 1621847

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A mixture of 5-(1-bromoethyl)-2-fluoropyridine (17.65 g, 87 mmol) and tert-butyl piperazine-1-carboxylate (16.92 g, 91 mmol) in acetonitrile (300 mL). was treated with potassium carbonate (14.35 g, 104 mmol) and potassium iodide (2.87 g, 17.30 mmol). The mixture was placed into a pre-heated (70° C.) bath and allowed to stir under inert atmosphere overnight. The reaction mixture was diluted with chloroform (200 mL) and water (100 mL). The organic layer was extracted with chloroform (3×50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was adsorbed onto a plug of silica gel and purified by chromatography through a silica-gel column (330 g) eluting with 50% ethyl acetate/hexanes to give tert-butyl 4-(1-(6-fluoropyridin-3-yl)ethyl)piperazine-1-carboxylate (17.27 g, 55.8 mmol, 64.5% yield) as a yellow oil. m/z (ESI, +ve ion) 310.1 (M+H)+.

Aufarbeitung

extractionThe organic layer was extracted with chloroform (3×50 mL)
dry with materialThe combined organic extracts were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by chromatography through a silica-gel column (330 g)
washeluting with 50% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag: ord-dbc40c577e724a9aaeebbec251cda902
Quelldatensatz: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08772480B2

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