Hydrochloric Acid → Pyridine, 3-(3-chloropropyl)-, hydrochloride

HRID 2309682Notes

Reaction equation

HRID 2309682 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9]O)[CH:2]=1.P(Cl)(Cl)([Cl:13])=O.[ClH:16]>C(OCC)(=O)C.[OH-].[Na+]>[ClH:13].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][Cl:16])[CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 178613-PyridinepropanolHCID 24813Phosphorus oxychloride

Product 1

HCID 205439Pyridine, 3-(3-chloropropyl)-, hydrochloride

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-(3-Pyridyl)propyl chloride hydrochloride was prepared in quantitative yield by reacting 3-(3-pyridyl)propanol with phosphorus oxychloride in ethyl acetate at reflux temperature. The free base was generated by dissolving the hydrochloride in a 10% sodium hydroxide solution and extracting with an organic solvent (toluene or ether).

Workup

  1. temperatureat reflux temperature
  2. extractionextracting with an organic solvent (toluene or ether)

Sources & evidence

ORD record
ord-65cf91a57628444487d9d93d49435361
Source dataset
uspto-grants-1987_09
Patent number
US04696920

Reaction notes

Loading…