Diethylamine → N-ethyl-N-[(4-nitrophenyl)methyl]ethanamine

HRID 492247Notes

Reaction equation

HRID 492247 reaction equation
[CH:1]1[C:6]([CH2:7]Br)=[CH:5][CH:4]=[C:3]([N+:9]([O-:11])=[O:10])[CH:2]=1.[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13]>CO>[CH2:12]([N:14]([CH2:15][CH3:16])[CH2:7][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[CH:2][CH:1]=1)[CH3:13]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 412435N-ethyl-N-[(4-nitrophenyl)methyl]ethanamineYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

P-nitrobenzyl bromide (5.0 g) was added to a methanol solution (50 mL) of diethylamine (16.9 g), and stirred at room temperature for 3 hours. Methanol was evaporated off from the reaction liquid under reduced pressure, and water was added to the resulting residue, and extracted with ethyl acetate. The organic layer was extracted with 1 N hydrochloric acid, and the aqueous layer was neutralized with aqueous ammonium solution. The aqueous layer was extracted with ethyl acetate, and the organic layer was dried with anhydrous magnesium sulfate, and then the solvent was evaporated off under reduced pressure to obtain N,N-diethyl-N-(4-nitrobenzyl)amine (4.8 g) as an orange oily substance.

Workup

  1. customMethanol was evaporated off from the reaction liquid under reduced pressure, and water
  2. additionwas added to the resulting residue
  3. extractionextracted with ethyl acetate
  4. extractionThe organic layer was extracted with 1 N hydrochloric acid
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  7. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-7954b13e1b8f497fab689d46018809ef
Source dataset
uspto-grants-2009_05
Patent number
US07531668B2

Reaction notes

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