Thionyl Chloride → 3-Chloro-2-chloromethyl-4-morpholin-4-yl-pyridinium chloride

HRID 1655209Notes

Reaction equation

HRID 1655209 reaction equation
S(Cl)([Cl:3])=O.[O:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([CH2:17]O)[C:12]=2[Cl:19])[CH2:7][CH2:6]1>C(Cl)(Cl)Cl>[ClH:3].[O:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([CH2:17][Cl:3])[C:12]=2[Cl:19])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19791250(3-Chloro-4-morpholinopyridin-2-yl)methanol

Product 1

HCID 197912463-Chloro-2-chloromethyl-4-morpholin-4-yl-pyridinium chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Thionyl chloride (3 ml) in chloroform (25 ml) was added dropwise to a solution of 4 -morpholino-3 -chloro-2 -hydroxymethylpyridine (3.09 g) in chloroform (25 ml) cooled in an ice/salt bath. Following the addition the ice bath was removed and the mixture stirred for a further 1.5 hours. The volume of the solution was reduced and ether added to give 4 -morpholino-3 -chloro-2 -chloromethylpyridine hydrochloride, 3.77 g, m.p. 200°-2°.

Workup

  1. temperaturecooled in an ice/salt bath
  2. customwas removed
  3. additionether added

Sources & evidence

ORD record
ord-2aa3f25670b1404e835b251d408a5229
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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