Hydrochloric Acid → [(6-Chloropyridin-2-yl)methyl]dimethylamine

HRID 1395531Notes

Reaction equation

HRID 1395531 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.Cl>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 876016-Chloro-2-picoline

Product 1

HCID 20434272[(6-Chloropyridin-2-yl)methyl]dimethylamineYield 42%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To 2-chloro-6-methylpyridine (38.3 g, 0.30 mole) in 300 ml of carbon tetrachloride is added N-bromosuccinimide (67.0 g, 0.375 mole) and benzoyl peroxide (1.0 g). The mixture is stirred at reflux for 22 hours. Then it is cooled to 10° and is filtered. Into the carbon tetrachloride solution of crude 2-chloro-6-bromomethylpyridine is bubbled dimethylamine with ice bath cooling. The mixture is allowed to stand at room temperature overnight. After removal of the dimethylamine hydrobromide by filtration the carbon tetrachloride filtrate is concentrated in vacuo to a dark oil. The oil is taken up in hexane and the product is extracted into 6 N hydrochloric acid (0.30 mole). The acid extract is made alkaline with sodium hydroxide and the product is extracted into benzene. After removal of the benzene the product is distilled. The yield is 42%, b.p. 108°-110° at 3.3 mm, n25D 1.5206.

Workup

  1. temperatureat reflux for 22 hours
  2. temperatureThen it is cooled to 10°
  3. filtrationis filtered
  4. customInto the carbon tetrachloride solution of crude 2-chloro-6-bromomethylpyridine is bubbled dimethylamine with ice bath
  5. temperaturecooling
  6. customAfter removal of the dimethylamine hydrobromide
  7. filtrationby filtration the carbon tetrachloride filtrate
  8. concentrationis concentrated in vacuo to a dark oil
  9. extractionThe acid extract
  10. extractionthe product is extracted into benzene
  11. customAfter removal of the benzene the product
  12. distillationis distilled

Sources & evidence

ORD record
ord-7fd3d9cd93de4a339cce395cbcd5af00
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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