Thionyl Chloride → HCID 21477483, compound

HRID 2293622Notes

Reaction equation

HRID 2293622 reaction equation
S(Cl)(Cl)=O.[ClH:5].[N:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]O)=[CH:8][CH:7]=1>C(Cl)(Cl)Cl>[Cl:5][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][N:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21477477HCID 21477477, compound

Product 1

HCID 21477483HCID 21477483, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

Thionyl chloride (1.03 ml) is added to 4-pyridinehexanol hydrochloride (2.42 g) and the mixture is stirred at 20° C. for 30 minutes. Excess saturated aqueous NaHCOs and CHCl3 (20 ml) is added. The organic phase is washed with saturated NaHCO3, brine and water, dried (MgSO4) and the solvent evaporated to give crude material which is purified by flash chromatography on silica gel (CH3OH:CHCl3 =1:49 by vol.) to give 4-(6-chlorohexyl)-pyridine as an oil.

Workup

  1. washThe organic phase is washed with saturated NaHCO3, brine and water
  2. dry with materialdried (MgSO4)
  3. customthe solvent evaporated
  4. customto give crude material which
  5. customis purified by flash chromatography on silica gel (CH3OH:CHCl3 =1:49 by vol.)

Sources & evidence

ORD record
ord-86ecff1e3e3a4a0aaecdf2cf0eca3328
Source dataset
uspto-grants-1997_11
Patent number
US05686564

Reaction notes

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