Potassium Carbonate → Tert-butyl 4-(3-chloropyridin-2-yl)piperazine-1-carboxylate

HRID 912763

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of 2,3-dichloropyridine (10 g, 67.5 mmol, Aldrich), tert-butyl 1-piperazinecarboxylate (12.58 g, 67.5 mmol, Aldrich), copper powder (0.5 g, 7.8 mmol) and K2CO3 (9.33 g, 67.5 mmol) in DMF (100 mL) was stirred at 120° C. for 16 h. The reaction mixture was cooled to room temperature, concentrated in vacuo and the residue was dissolved in EtOAc (200 mL). The organic solution was washed with saturated aqueous solution of NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4, and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography, eluting with 15% EtOAc/hexane, to give the title compound as an orange oil. MS (ESI, pos. ion) m/z: 298 (M+1).

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
dissolutionthe residue was dissolved in EtOAc (200 mL)
washThe organic solution was washed with saturated aqueous solution of NaHCO3 (50 mL) and brine (50 mL)
dry with materialdried over Na2SO4
filtrationfiltered
customThe solvent was removed in vacuo
customthe residue was purified by silica gel column chromatography
washeluting with 15% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag: ord-525e89e0db04423b8ae69121722b1efc
Quelldatensatz: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08026241B2

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