Diethylamine → HCID 70622255, compound

HRID 1605580Notes

Reaction equation

HRID 1605580 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[C:6]([NH:9][C:10]1[C:17]([CH2:18][CH2:19]Br)=[CH:16][C:15]([Br:21])=[CH:14][C:11]=1CBr)(=[O:8])[CH3:7]>C(Cl)(Cl)(Cl)Cl>[C:6]([NH:9][C:10]1[C:11]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:14][C:15]([Br:21])=[CH:16][C:17]=1[CH:18]([CH3:19])[N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 54315337HCID 54315337, compound

Product 1

HCID 70622255HCID 70622255, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

24 gm of diethylamine were added to a solution of 16.5 gm of 2-acetylamino-5-bromo-3-bromoethyl-benzyl bromide in 1.6 liters of carbon tetrachloride, and the mixture was refluxed for 1 hour. Subsequently, the reaction solution was evaporated, the residue was dissolved in 0.7 liter of 2 N hydrochloric acid, and the solution was extracted twice with chloroform. The hydrochloric acid phase was made alkaline with concentrated ammonia and extracted three times with chloroform. The organic phase was dried with sodium sulfate, and the solvent was distilled off. The residue was purified by column-chromatography on silicagel with ethylacetate/methanol (1:1), the corresponding fractions were united, and 2-acetylamino-5-bromo-N,N-diethyl-3-diethylamino-methyl-benzylamine, m.p. 91.5°-93°C, was obtained by recrystallization from petroleum ether.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. customSubsequently, the reaction solution was evaporated
  3. dissolutionthe residue was dissolved in 0.7 liter of 2 N hydrochloric acid
  4. extractionthe solution was extracted twice with chloroform
  5. extractionextracted three times with chloroform
  6. dry with materialThe organic phase was dried with sodium sulfate
  7. distillationthe solvent was distilled off
  8. customThe residue was purified by column-chromatography on silicagel with ethylacetate/methanol (1:1)

Sources & evidence

ORD record
ord-0a10f5925ff34cc285b570ac175b3113
Source dataset
uspto-grants-1976_04
Patent number
US03950393

Reaction notes

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