Chloroform → 4-(3-Chloropropyl)pyridyl hydrochloride

HRID 1384523Notes

Reaction equation

S(Cl)([Cl:3])=O.[N:5]1C=[CH:9][C:8]([CH2:11][CH2:12][CH2:13]O)=[CH:7][CH:6]=1.Cl[CH:16]([Cl:18])Cl>>[Cl:3][CH2:13][CH2:12][CH2:11][C:8]1[CH:7]=[CH:6][N:5]=[C:16]([Cl:18])[CH:9]=1

Participants

Reactant 3

HCID 6212Chloroform

HCID 24386Thionyl Chloride

HCID 729234-Pyridinepropanol

Product 1

HCID 865846804-(3-Chloropropyl)pyridyl hydrochloride

Conditions

Temperature: 0 °C

Procedure

Thionyl chloride (1.6 ml) was added to a solution of 4-pyridine propanol (2 g, 14.5 mmol) in trichloromethane (20 ml) cooled at 0° C. After stirring for 1 hour at ambient temperature followed by 1 hour at 60° C., the solvent was evaporated and the residue was triturated with ether to give 4-(3-chloropropyl)pyridyl hydrochloride as a white solid. 1H NMR Spectrum: (DMSOd6) 2.15(m, 2H); 3.02(t, 2H); 3.69(t, 2H); 7.96(d, 2H); 8.84(d, 2H)

Workup

waitfollowed by 1 hour at 60° C.
customthe solvent was evaporated
customthe residue was triturated with ether

Sources & evidence

ORD record: ord-37c9eac146a04d6c9f722b1c97ec3952
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06258951B1

Reaction notes

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