Thionyl Chloride → 4-(3-Chloropropyl)pyridine

HRID 2258446Notes

Reaction equation

HRID 2258446 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9]O)=[CH:3][CH:2]=1.S(Cl)([Cl:13])=O>C(Cl)(Cl)Cl>[Cl:13][CH2:9][CH2:8][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 729234-Pyridinepropanol

Product 1

HCID 2054424-(3-Chloropropyl)pyridineYield 96.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 3-(4-pyridyl)propanol (22.05 g, 0.16 mol) in 100 mL of dry chloroform (CHCl3) at 0° C. was added dropwise a CHCl3 solution of thionylchloride (SOCl2, 17.5 mL, 0.24 mol). The reaction was allowed to warm to room temperature, stirred for 1 hour, and then brought to reflux for 1 hour. After cooling the reaction to room temperature, it was stripped of all solvent under reduced pressure and the residue was partitioned between CH2Cl2 and water that had been made basic with concentrated NH4OH. The aqueous phase was washed 2× with CH2Cl2 and the combined organic phase was dried (Na2SO4), filtered, and stripped of solvent to yield 24 g of crude product. This material was vacuum distilled at 68°-71° C. (0.3 mm) to give 24 g of the title compound.

Workup

  1. temperatureto reflux for 1 hour
  2. temperatureAfter cooling
  3. customthe reaction to room temperature
  4. customthe residue was partitioned between CH2Cl2 and water that
  5. washThe aqueous phase was washed 2× with CH2Cl2
  6. dry with materialthe combined organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. customto yield 24 g of crude product
  9. distillationdistilled at 68°-71° C. (0.3 mm)

Sources & evidence

ORD record
ord-99783c14e55f4187b480efbe1cb7f397
Source dataset
uspto-grants-1997_08
Patent number
US05661146

Reaction notes

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