2-(Methylamino)ethanol → HCID 22030569, compound

HRID 1782063Notes

Reaction equation

HRID 1782063 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[CH3:6][O:7][CH2:8][CH2:9]Br.C(N(CC)CC)C>C(#N)C>[CH3:6][O:7][CH2:8][CH2:9][N:2]([CH2:3][CH2:4][OH:5])[CH3:1]

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 8471TriethylamineHCID 809722-Bromoethyl methyl ether

Product 1

HCID 22030569HCID 22030569, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-methylaminoethanol (5.4 g), 2-bromoethyl methyl ether (10 g), triethylamine (10 ml) and acetonitrile (70 ml) was stirred and heated to reflux for 16 hours. The mixture was cooled to ambient temperature and filtered. The filtrate was evaporated and the residue was triturated under diethyl ether. The organic solution was separated and evaporated to give 2-[N-(2-methoxyethyl)-N-methylamino]ethanol (3 g, 31%); NMR Spectrum: (CDCl3) 2.35 (s, 3H), 2.6 (t, 2H), 2.65 (t, 2H), 3.35 (s, 3H), 3.5 (t, 2H), 3.6 (t, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe residue was triturated under diethyl ether
  6. customThe organic solution was separated
  7. customevaporated

Sources & evidence

ORD record
ord-2ee3af91388349f0b7cf2785f42332cf
Source dataset
uspto-grants-2009_03
Patent number
US07498335B2

Reaction notes

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