Tetrahydrofuran → N,N-dimethyl-2-[methyl-(2-pyridine-4-yl-ethyl)-amino]-acetamide

HRID 346518Notes

Reaction equation

HRID 346518 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.[CH3:11][N:12]([CH3:17])[C:13](=[O:16])[CH2:14]Cl.C(=O)(O)[O-].[Na+].O1CCCC1>CO>[CH3:11][N:12]([CH3:17])[C:13](=[O:16])[CH2:14][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 758862-chloro-N,N-dimethylacetamideHCID 143276Methyl[2-(pyridin-4-yl)ethyl]amineHCID 516892Sodium Bicarbonate

Product 1

HCID 21081298N,N-dimethyl-2-[methyl-(2-pyridine-4-yl-ethyl)-amino]-acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-[2-(methylamino)ethyl]pyridine (34.4 g) and 29.18 g of chloroacetic acid-dimethylamide are dissolved in 200 ml of methanol. After the addition of 20 g of sodium bicarbonate the mixture is refluxed for 5 hours with stirring. For working up the mixture is combined with 1000 ml of tetrahydrofuran, decanted off from the precipitated salts and the solution is filtered through active charcoal. After the limination of the solvent, N,N-dimethyl-2-[methyl-(2-pyridine-4-yl-ethyl)-amino]-acetamide is obtained as a crude product.

Workup

  1. temperatureis refluxed for 5 hours
  2. customdecanted off from the precipitated salts
  3. filtrationthe solution is filtered through active charcoal

Sources & evidence

ORD record
ord-8518d2a82ffc4bf1a35ec31a6d3692e5
Source dataset
uspto-grants-2007_02
Patent number
US07173028B2

Reaction notes

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