Dichloromethane → (3-Chloro-2-chloromethylpyridin-4-yl)-(2-chloroethyl)methylamine hydrochloride

HRID 1378313Notes

Reaction equation

HRID 1378313 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:7](CO)=[N:8][CH:9]=[CH:10][C:11]=1[N:12]([CH2:14][CH2:15]O)[CH3:13].Cl[CH2:20][Cl:21]>>[ClH:3].[Cl:5][C:6]1[C:7]([CH2:20][Cl:21])=[N:8][CH:9]=[CH:10][C:11]=1[N:12]([CH2:14][CH2:15][Cl:3])[CH3:13]

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 24386Thionyl ChlorideHCID 537528042-[(3-Chloro-2-hydroxymethyl-pyridin-4-yl)-methylamino]-ethanol

Product 1

HCID 22117349(3-Chloro-2-chloromethylpyridin-4-yl)-(2-chloroethyl)methylamine hydrochloride

Procedure

A solution of thionyl chloride (4 ml) in dichloromethane (20 ml) is added dropwise to a solution of 3-chloro-4-[N-(2-hydroxyethyl)-N-methylamino]-2-hydroxymethylpyridine (2.3 g) in dichloromethane (30 ml) at 0° C. The temperature is then allowed to rise to 20° C. (20 min), and then the temperature is kept at 40° C. for 30 min. The solvent is stripped off in vacuo and then the remaining residue is chromatographed on silica gel (petroleum ether/ethyl acetate 7/3 mixture which contains 1 ml of conc. NH3 ×aq/l). Yield: 2.6 g.

Workup

  1. customto rise to 20° C.
  2. custom(20 min)
  3. customthe remaining residue is chromatographed on silica gel (petroleum ether/ethyl acetate 7/3 mixture which contains 1 ml of conc. NH3 ×aq/l)

Sources & evidence

ORD record
ord-99e97644018941669c6e8b19fd716399
Source dataset
uspto-grants-1997_09
Patent number
US05668131

Reaction notes

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