Thionyl Chloride → 2-Chloromethyl-4-dimethylaminomethylpyridine dihydrochloride

HRID 364999Notes

Reaction equation

HRID 364999 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11]O)[CH:6]=1)[CH3:3].S(Cl)([Cl:15])=O>ClCCl>[ClH:15].[ClH:15].[Cl:15][CH2:11][C:7]1[CH:6]=[C:5]([CH2:4][N:2]([CH3:3])[CH3:1])[CH:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 132926014-Dimethylaminomethyl-2-hydroxymethylpyridine

Product 1

HCID 132926032-Chloromethyl-4-dimethylaminomethylpyridine dihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Dimethylaminomethyl-2-hydroxymethylpyridine (13.45 g) in dichloromethane (200 ml) was added dropwise to a stirred solution of thionyl chloride (30 ml) in dichoromethane (150 ml). The resulting red mixture was stirred for 1 hour then concentrated in vacuo. The residue was treated with ether (300 ml) to yield a crystalline solid. Recrystallisation from methanol/ether (1:3) yielded 2-chloromethyl-4-dimethylaminomethylpyridine dihydrochloride (20.04 g) as an orange solid m.p. 202°-204°.

Workup

  1. concentrationthen concentrated in vacuo
  2. additionThe residue was treated with ether (300 ml)
  3. customto yield a crystalline solid
  4. customRecrystallisation from methanol/ether (1:3)

Sources & evidence

ORD record
ord-177582f404ff4cd5b29f142faed030b6
Source dataset
uspto-grants-1986_08
Patent number
US04607107

Reaction notes

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