Thionyl Chloride → 3-(Chloromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine hydrochloride

HRID 856787Notes

Reaction equation

HRID 856787 reaction equation
[N:1]1[CH:2]=[C:3]([CH2:10]O)[N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=12.S(Cl)([Cl:14])=O>>[ClH:14].[Cl:14][CH2:10][C:3]1[N:4]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]2=[N:1][CH:2]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 229385385,6,7,8-Tetrahydroimidazo[1,2-a]pyridin-3-ylmethanol

Product 1

HCID 229385113-(Chloromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine hydrochloride

Procedure

To 5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-3-yl methanol (1.0 g), thionyl chloride (5 ml) was added at 0° C. After heating to reflux for 40 minutes, the mixture was concentrated under reduced pressure. To the residue was added ethyl acetate, and the precipitated crystals were collected by filtration. The crystals were washed with ethyl acetate, to give 3-(chloromethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine hydrochloride (1.03 g) as pale yellow crystals.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 40 minutes
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionTo the residue was added ethyl acetate
  5. filtrationthe precipitated crystals were collected by filtration
  6. washThe crystals were washed with ethyl acetate

Sources & evidence

ORD record
ord-5a113966d87b4507ad2682dc12a781c3
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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