Reaction #69982

Reaction equation

4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

sodium tert-butoxide

1-bromo-4-iodobenzene

4-(piperidin-4-yloxy)pyridine

→

4-[1-(4-bromophenyl)piperidin-4-yloxy]pyridine

Yield 50.9%

Solvents

Ethyl acetate

toluene

Conditions

Workup

1. 1
   Washthe mixture is washed twice with water and once with a saturated aqueous sodium chloride solution
2. 2
   DryingThe organic phase is dried over magnesium sulphate
3. 3
   Concentrationconcentrated under reduced pressure
4. 4
   OtherThe crude product obtained
5. 5
   Otheris chromatographed on silica gel, elution

Procedure

2 g of 1-bromo-4-iodobenzene and 1.386 g of 4-(piperidin-4-yloxy)pyridine are placed in 35 ml of toluene and then 0.324 g of tris(dibenzylideneacetone)dipalladium(0), 0.245 g of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene and 1.019 g of sodium tert-butoxide are added. The reaction medium is heated at 110° C. for 18 h. Ethyl acetate is subsequently added and the mixture is washed twice with water and once with a saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate and concentrated under reduced pressure. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of a dichloromethane/methanol (99/1 to 98/2) mixture. 1.2 g of 4-[1-(4-bromophenyl)piperidin-4-yloxy]pyridine are obtained.

Source