Benzyl Bromide → 2-(1-Benzyl-1,2,5,6-tetrahydropyridin-3-yl)-2-methyl-1,3-dioxolane

HRID 1029618Notes

Reaction equation

HRID 1029618 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]1([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[O:14][CH2:13][CH2:12][O:11]1>CC(C)=O>[CH2:1]([N:17]1[CH2:18][CH2:19][CH:20]=[C:15]([C:10]2([CH3:9])[O:11][CH2:12][CH2:13][O:14]2)[CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 2807153-(2-Methyl-1,3-dioxolan-2-yl)pyridine

Product 1

HCID 151172232-(1-Benzyl-1,2,5,6-tetrahydropyridin-3-yl)-2-methyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyl bromide (9.8 ml) was added to a solution of 2-methyl-2-(pyridin-3-yl)-1,3-dioxolane (13.6 g) in acetone (140 ml) and the mixture was refluxed. After confirming the disappearance of the starting material, the acetone was distilled off under reduced pressure. The residue was dissolved in ethanol (140 ml) and while the solution was ice-cooled, sodium borohydride (3.12 g) was gradually added. After the mixture was stirred for 1 hour, water and ethyl acetate were added. The mixture was stirred and, then, allowed to stand. The aqueous layer was separated and extracted with 2 portions of ethyl acetate. The organic layers were combined, washed successively with saturated aqueous sodium hydrogen carbonate solution, water and aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. Finally the solvent was distilled off under reduced pressure to give 2-(1-benzyl-1,2,5,6-tetrahydropyridin-3-yl)-2-methyl-1,3-dioxolane (7.86 g).

Workup

  1. temperaturethe mixture was refluxed
  2. distillationthe acetone was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in ethanol (140 ml) and while the solution
  4. temperaturecooled
  5. additionsodium borohydride (3.12 g) was gradually added
  6. additionwater and ethyl acetate were added
  7. stirringThe mixture was stirred
  8. customThe aqueous layer was separated
  9. extractionextracted with 2 portions of ethyl acetate
  10. washwashed successively with saturated aqueous sodium hydrogen carbonate solution, water and aqueous sodium chloride solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationFinally the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0213c13a74f9448cb0e4792a4e9594e3
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

Loading…