Sodium Chloride → N-Methyl-2-(pyridin-3-YL)ethanamine

HRID 249478Notes

Reaction equation

HRID 249478 reaction equation
[CH3:1][NH2:2].Cl.[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11]Cl)[CH:5]=1.[OH-].[Na+].[Cl-].[Na+]>>[CH3:1][NH:2][CH2:11][CH2:10][C:6]1[CH:5]=[N:4][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 6329MethylamineHCID 14798Sodium HydroxideHCID 199465Pyridine, 3-(2-chloroethyl)-, hydrochloride

Product 1

HCID 5152594N-Methyl-2-(pyridin-3-YL)ethanamineYield 110.5%

Conditions

Temperature
80 °C

Procedure

To 32.6 g of 40% aqueous methylamine solution was added 7.48 g (0.042 mole) of 2-(3-pyridyl)ethyl chloride hydrochloride in small portions with stirring. The mixture was transfered to a stainless steel reaction column and heated at an external temperature of 80° C. for 4 hours. After cooling, 3.36 g of NaOH was added with ice-cooling and stirring and the mixture was saturated with sodium chloride and extracted with CH2Cl2. The extract was dried over MgSO4 and the CH2Cl2 was distilled off to give 6.32 g of the title compound in crude form as a yellow oil.

Workup

  1. temperatureAfter cooling
  2. temperaturecooling
  3. stirringstirring
  4. extractionextracted with CH2Cl2
  5. dry with materialThe extract was dried over MgSO4
  6. distillationthe CH2Cl2 was distilled off

Sources & evidence

ORD record
ord-dbb7fe6b4f0c445f834aa9bd274f8366
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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