Benzoyl Peroxide → 2-Chloro-6-(piperidin-1-ylmethyl)pyridine

HRID 370541Notes

Reaction equation

HRID 370541 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.BrN1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[N:3]=1

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 8082PiperidineHCID 67184N-bromobutanimideHCID 876016-Chloro-2-picoline

Product 1

HCID 133886862-Chloro-6-(piperidin-1-ylmethyl)pyridineYield 41%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To 2-chloro-6-methylpyridine (50.0 g, 0.392 mole) in 393 mL of carbon tetrachloride was added N-bromosuccinimide (87.2 g, 0.49 mole) and 1.0 g of benzoyl peroxide. The mixture was stirred at reflux for 22 hours, cooled to 10° and filtered. The chilled filtrate then was treated slowly with piperidine (83.5 g, 0.98 mole) and allowed to stir at ambient temperature for 18 hours. After removal of the piperidine hydrobromide by filtration, the filtrate was concentrated to about half volume and extracted with 6N HCl (65 mL) and 3N HCl (40 mL). The acid extracts were made basic with 40% sodium hydroxide and the product was extracted into methylene chloride. The solvent was evaporated and the residue distilled to yield 41% of the title compound as a colorless oil, b.p. 101°-103°/0.45 mm Hg.

Workup

  1. temperatureat reflux for 22 hours
  2. temperaturecooled to 10°
  3. filtrationfiltered
  4. stirringto stir at ambient temperature for 18 hours
  5. customAfter removal of the piperidine hydrobromide
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated to about half volume
  8. extractionextracted with 6N HCl (65 mL) and 3N HCl (40 mL)
  9. extractionthe product was extracted into methylene chloride
  10. customThe solvent was evaporated
  11. distillationthe residue distilled

Sources & evidence

ORD record
ord-ab75ff4a0a7a4d478685daa878ed99d9
Source dataset
uspto-grants-1985_07
Patent number
US04526973

Reaction notes

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