[N+](C1C=CC(C2C=CC(C(NCCCCC3C=NC=CC=3)=O)=CC=2)=CC=1)([O-])=O.S(Cl)([Cl:31])=O.[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]O.[OH-].[Na+]>ClCCl>[Cl:31][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][N:33]=1A solution of 4 1 mL of thionyl chloride in 30 mL of dichloromethane was added over 10 minutes to a stirred solution of 6.65 g of 2-pyridinepentanol in 60 mL of dichloromethane maintained at -5° C. After the addition was complete. the mixture was stirred at room temperature for 17 hours, then was rechilled to 5° C. as 150 ml of 1N NaOH was added droPwise over 10 minutes. The layers were separated and the aqueous layer was extracted with 75 mL of dichloromethane. The organic layers were washed with brine, then were combined. dried (K2CO3) and evaporated to yield 7.4 g of 2-(5-chloropentyl)pyridine as an oil.
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