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

HRID 1275574Notes

Reaction equation

HRID 1275574 reaction equation
[Cl:1][C:2]1[C:3](CO)=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([CH2:10][CH2:11]O)[CH3:9].S(Cl)([Cl:17])=O.Cl[CH2:20][Cl:21]>>[ClH:1].[Cl:1][C:2]1[C:3]([CH2:20][Cl:21])=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([CH2:10][CH2:11][Cl:17])[CH3:9]

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 3-chloro-4-[N-(2-hydroxyethyl)-N-methylamino]-2-hydroxymethylpyridine (2.3 g) in dichloromethane (30 ml) is treated dropwise at 0° C. with a solution of thionyl chloride (4 ml) in dichloromethane (20 ml). The temperature is then allowed to climb to 20° C. (20 min) and the temperature is then kept at 400° C. for 30 min. After stripping off the solvent in vacuo, the residue which remains 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 climb to 20° C.
  2. custom(20 min)
  3. customthe residue which remains 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-b084d3573474413cb9664f69b9e4505e
Source dataset
uspto-grants-2000_12
Patent number
US06162809

Reaction notes

Loading…