N-bromobutanimide → 3-Bromo-2,6-bis(2,2,6,6-tetramethylpiperidin-1-yl)pyridine

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Reaktionsgleichung

[CH3:1][C:2]1([CH3:26])[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[N:3]1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[C:21]([CH3:23])([CH3:22])[CH2:20][CH2:19][CH2:18][C:17]2([CH3:25])[CH3:24])[N:11]=1.C1C(=O)N([Br:34])C(=O)C1>C(#N)C>[Br:34][C:13]1[C:12]([N:16]2[C:17]([CH3:25])([CH3:24])[CH2:18][CH2:19][CH2:20][C:21]2([CH3:23])[CH3:22])=[N:11][C:10]([N:3]2[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][CH2:7][C:2]2([CH3:26])[CH3:1])=[CH:15][CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Reaction was performed under air. To a ice-cooled solution of 2,6-bis(2,2,6,6-tetramethylpiperidin-1-yl)pyridine (1 g, 2.8 mmol) in acetonitrile (100 ml) was added NBS (0.45 g, 2.5 mmol) portion-wise over 30 min. The reaction mixture was stirred at −0° C. for 2 h, until the color of the solution disappeared and then stirred overnight at room temperature. The reaction was quenched with water (100 mL) and the product extracted by ethylacetate. The product was purified by column chromatography on silica gel and obtained as white solid (Rf=0.6 in Ethylacetate:hexane=1:20, Yield=0.53 g (43.4%))

Aufarbeitung

customReaction
stirringstirred overnight at room temperature
customThe reaction was quenched with water (100 mL)
extractionthe product extracted by ethylacetate
customThe product was purified by column chromatography on silica gel
customobtained as white solid (Rf=0.6 in Ethylacetate:hexane=1:20, Yield=0.53 g (43.4%))

Quellen und Nachweise

ORD-Eintrag: ord-fb258cc5b09d49c08ff22131f138f795
Quelldatensatz: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09269912B2

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