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

HRID 1076675Notes

Reaction equation

HRID 1076675 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-34ea3ddc8149425297a7e7ef1168175d
Source dataset
uspto-grants-1976_05
Patent number
US03957793

Reaction notes

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