Benzyl Chloride → 1-Benzyl-3,4-diethylpyridin-1-ium chloride

HRID 917862Notes

Reaction equation

HRID 917862 reaction equation
[CH2:1]([Cl:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[CH2:17][CH3:18])[CH3:10]>C(O)(C)C>[Cl-:8].[CH2:1]([N+:13]1[CH:14]=[CH:15][C:16]([CH2:17][CH3:18])=[C:11]([CH2:9][CH3:10])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 691513,4-Diethylpyridine

Product 1

HCID 203381101-Benzyl-3,4-diethylpyridin-1-ium chloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Benzyl chloride (250 g.) was added dropwise to a solution of 3,4-diethylpyridine (262 g., Beilsteins Handbuch der Organischen Chemie, Vierte Auflage, Julius Springer, Berlin, 1935 p. 253) in isopropyl alcohol (700 ml.). The resulting solution was refluxed (for 2 hr.), then concentrated under water pump vacuum. Benzene (250 ml.) was added to the residue and the solution was concentrated again. The process was repeated with two further portions (250 ml. and 500 ml.) of benzene. The residue began to crystallize. Benzene (2250 ml.) was added, affording a thick slurry of 1-benzyl-3,4-diethylpyridinium chloride.

Workup

  1. temperatureThe resulting solution was refluxed (for 2 hr.)
  2. concentrationconcentrated under water
  3. additionBenzene (250 ml.) was added to the residue
  4. concentrationthe solution was concentrated again
  5. customto crystallize
  6. additionBenzene (2250 ml.) was added

Sources & evidence

ORD record
ord-49ea20c0cf2743619ad0f415a4453e86
Source dataset
uspto-grants-1976_07
Patent number
US03968114

Reaction notes

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