Bis(2-Methoxyethyl)amine → HCID 23507503, compound

HRID 1388060Notes

Reaction equation

HRID 1388060 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][O:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][O:19][CH3:20].C(N(CC)CC)C>C1COCC1>[CH3:12][O:13][CH2:14][CH2:15][N:16]([CH2:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH2:17][CH2:18][O:19][CH3:20]

Participants

5

Reactant 3

HCID 2383Bis(2-Methoxyethyl)amineHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 23507503HCID 23507503, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of p-nitrobenzyl bromide (10 g) in THF (50 ml) was added dropwise to a solution of bis(2-methoxyethyl)-amine (6.8 g) and triethylamine (10 ml) in THF (50 ml). Under nitrogen atmosphere, the mixture was stirred at room temperature overnight, and the solvent was evaporated. To the residue was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated to give N,N-bis(2-methoxyethyl)-4-nitrobenzylamine (10.8 g) as yellow oil.

Workup

  1. customthe solvent was evaporated
  2. additionTo the residue was added water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-28a4b9d325c747789735477f16be607e
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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