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

HRID 1779136Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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%))

Workup

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%))

Sources & evidence

ORD record: ord-fb258cc5b09d49c08ff22131f138f795
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09269912B2

Reaction notes

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