Imidazole → 2-(1H-imidazol-1-ylmethyl)pyridine

HRID 370653Notes

Reaction equation

HRID 370653 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.CC(C)([O-])C.[K+].[NH:16]1[CH:20]=[CH:19][N:18]=[CH:17]1>C(O)C.C(O)CCC>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 23392Picolyl chloride hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 3276652-(1H-imidazol-1-ylmethyl)pyridine

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 702EthanolSolvent

Procedure

A solution of 2-chloromethylpyridine hydrochloride (16.4 g, 0.1 mol) in ethanol (50 ml) was added dropwise to a stirred, boiling solution of potassium tert-butoxide (22.4 g, 0.2 mol) and imidazole (6.8 g, 0.1 mol) in dry butan-1-ol (100 ml). Following the addition, the reaction mixture was stirred and heated under reflux for 5 h. After removal of the solvents under reduced pressure, the resulting oil was dissolved in hydrochloric acid (150 ml, 2M), and the acid solution was washed with ether (100 ml). The acid solution was then basified with sodium hydroxide solution (10M), and the basic solution was extracted with chloroform (3×100 ml). The chloroform solutions were combined, dried (MgSO4), and the chloroform was then removed under reduced pressure. The residue was purified by using a silica-gel column and by elution with chloroform/methanol (9:1). The resulting solid was recrystallised from ethanol/light petroleum affording 1-(2-pyridylmethyl)imidazole as white cubes m.p. 79°-80°.

Workup

  1. additionthe addition
  2. temperatureheated
  3. temperatureunder reflux for 5 h
  4. customAfter removal of the solvents under reduced pressure
  5. dissolutionthe resulting oil was dissolved in hydrochloric acid (150 ml, 2M)
  6. washthe acid solution was washed with ether (100 ml)
  7. extractionthe basic solution was extracted with chloroform (3×100 ml)
  8. dry with materialdried (MgSO4)
  9. customthe chloroform was then removed under reduced pressure
  10. customThe residue was purified
  11. washby elution with chloroform/methanol (9:1)
  12. customThe resulting solid was recrystallised from ethanol/light petroleum

Sources & evidence

ORD record
ord-dd2ed5151afc431f8a687f1607de0813
Source dataset
uspto-grants-1985_07
Patent number
US04528195

Reaction notes

Loading…