Benzoyl Peroxide → HCID 68297534, compound

HRID 1411075Notes

Reaction equation

HRID 1411075 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[N:7]([CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:6]=1[CH3:19])=[O:4].[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([Br:11])[C:8](=[O:12])[N:7]([CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:6]=1[CH2:19][Br:20])=[O:4]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 68297539HCID 68297539, compound

Product 1

HCID 68297534HCID 68297534, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-bromo-1-cyclopentylmethyl-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid methyl ester (4.46 g, 13.6 mmol), N-bromosuccinimide (2.66 g, 15.0 mmol), and benzoyl peroxide (0.33 g, 1.36 mmol) in CCl4 (130 mL) was refluxed for 16 h. The resulting suspension was filtered, and the filtrate was evaporated in vacuo. The residue was purified by silica gel chromatography (0-25% EtOAc/hexanes) to give 2.5 g of the title compound. MS: (+) m/z 408.10 (M+1).

Workup

  1. temperaturewas refluxed for 16 h
  2. filtrationThe resulting suspension was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by silica gel chromatography (0-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-23f5862234d2418b856d1d94ab450e68
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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