2-(Methylamino)ethanol → 2-(N-(2,6-dimethyl-4-pyridyl)-N-methylamino)ethanol

HRID 1384592Notes

Reaction equation

HRID 1384592 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[CH:3]=1.[CH3:10][NH:11][CH2:12][CH2:13][OH:14]>Cl.O>[CH3:8][C:6]1[CH:7]=[C:2]([N:11]([CH2:12][CH2:13][OH:14])[CH3:10])[CH:3]=[C:4]([CH3:9])[N:5]=1

Participants

5

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 5881754-Chloro-2,6-dimethylpyridine

Product 1

HCID 226250732-(N-(2,6-dimethyl-4-pyridyl)-N-methylamino)ethanolYield 90%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

A solution of 4-chloro-2,6-dimethylpyridine (849 mg, 6 mmol), (J. Het. Chem. 1990, 1841), in 2-(methylamino)ethanol (1.35 g, 18 mmol) and 3M ethereal hydrogen chloride (3 drops) was heated at 140° C. for 1 hour. The reaction mixture was allowed to cool and was diluted with water. The insolubles were removed by filtration and the aqueous filtrate was poured onto a suspension of magnesium sulphate (50 g) in ethyl acetate (100 ml). The insolubles were removed by filtration and the filtrate dried (MgSO4) and the solvent removed by evaporation. The solid residue was triturated with ether, collected by filtration and dried under vacuum at 50° C. to give 2-(N-(2,6-dimethyl-4-pyridyl)-N-methylamino)ethanol (960 mg, 90%). m.p. 139-144° C. 1H NMR Spectrum: (CDCl3) 2.4(s, 6H); 3.0(s, 3H); 3.51(t, 2H); 3.81(t, 2H); 6.26(s, 2H) MS-ESI: 181 [MH]+

Workup

  1. temperatureto cool
  2. customThe insolubles were removed by filtration
  3. additionthe aqueous filtrate was poured onto a suspension of magnesium sulphate (50 g) in ethyl acetate (100 ml)
  4. customThe insolubles were removed by filtration
  5. dry with materialthe filtrate dried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe solid residue was triturated with ether
  8. filtrationcollected by filtration
  9. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-b4d3e26ece064070b889e303009f23a4
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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