[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]=13-(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).
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