Isopropanol → 1-Benzyl-3,4-dimethylpyridin-1-ium chloride

HRID 1975314Notes

Reaction equation

HRID 1975314 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[C:3]([CH3:8])[CH:2]=1.[CH2:9]([Cl:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)(C)C>CCOCC>[Cl-:16].[C:10]1([CH2:9][N+:1]2[CH:6]=[CH:5][C:4]([CH3:7])=[C:3]([CH3:8])[CH:2]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 7503Benzyl ChlorideHCID 114173,4-Dimethylpyridine

Product 1

HCID 139786171-Benzyl-3,4-dimethylpyridin-1-ium chlorideYield 76.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3,4-lutidine (112 mL, 1.0 mole), benzyl chloride (115 mL, 1.0 mole) and isopropanol (500 mL) was refluxed under nitrogen for 5 hours and then was stirred at room temperature for 60 hours. The mixture was diluted with ether and the resulting white precipitate was filtered and dried to afford 178.3 g (76%) of N-(phenylmethyl)-3,4-dimethylpyridinium chloride.

Workup

  1. temperaturewas refluxed under nitrogen for 5 hours
  2. filtrationthe resulting white precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-8031e33ee2264bb4aed4946663898cf8
Source dataset
uspto-grants-1994_02
Patent number
US05286733

Reaction notes

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