Benzoyl Peroxide → [(6-Chloropyridin-2-yl)methyl]dimethylamine

HRID 1154694Notes

Reaction equation

HRID 1154694 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.Br[N:10]1[C:14](=O)CC[C:11]1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:10]([CH3:14])[CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide2×HCID 876016-Chloro-2-picoline

Product 1

HCID 20434272[(6-Chloropyridin-2-yl)methyl]dimethylamine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Chloro-6-methylpyridine (6.4 g, 0.05 mol) is refluxed with N-bromosuccinimide (8.9 g, 0.05 mol) in 50 ml of carbon tetrachloride with benzoyl peroxide (50 mg) until the N-bromosuccinimide has reacted completely (7-14 hours). The succinimide is removed by filtering and the filtrate is saturated with anhydrous dimethylamine. Dimethylamine hydrochloride is removed by filtration and the filtrate is concentrated in vacuo. The residual oil is taken up in hexane and extracted into dilute hydrochloric acid. After the acid extract is washed with ether it is made basic with sodium hydroxide and extracted with ether. The ether extract is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. This gives 2.2 g of 2-chloro-6-dimethylaminomethylpyridine as a pale yellow oil.

Workup

  1. customhas reacted completely (7-14 hours)
  2. customThe succinimide is removed
  3. filtrationby filtering
  4. customDimethylamine hydrochloride is removed by filtration
  5. concentrationthe filtrate is concentrated in vacuo
  6. extractionextracted into dilute hydrochloric acid
  7. extractionAfter the acid extract
  8. washis washed with ether it
  9. extractionextracted with ether
  10. extractionThe ether extract
  11. dry with materialis dried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a37af2f2be57484fac4fbe425a509bf9
Source dataset
uspto-grants-1984_12
Patent number
US04490533

Reaction notes

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