Diethylamine → HCID 19907473, compound

HRID 2371536Notes

Reaction equation

HRID 2371536 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15]Br)=[CH:8][CH:7]=1.[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18]>C(O)C>[CH2:17]([N:19]([CH2:20][CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][N:19]([CH2:20][CH3:21])[CH2:17][CH3:18])=[CH:8][CH:7]=1)[CH3:18]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 15284075HCID 15284075, compound

Product 1

HCID 19907473HCID 19907473, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

First, 1.05 g of 1,4-bis(4-bromobutyl)benzene and 1.1 g of diethylamine were dissolved in absolute ethanol, and the mixture was refluxed for an hour and then evaporated under a reduced pressure to remove the solvent. After adding chloroform, the mixture was evaporated under a reduced pressure. After adding ethyl acetate the mixture was extracted with 15 ml of 1N hydrochloric acid. The aqueous extract was alkalized with 10% sodium hydroxide, and extracted with total 70 ml of chloroform. The organic extract was washed with water and a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated under a reduced pressure to obtain 0.70 g of the title compound as a colorless liquid.

Workup

  1. temperaturethe mixture was refluxed for an hour
  2. customevaporated under a reduced pressure
  3. customto remove the solvent
  4. additionAfter adding chloroform
  5. customthe mixture was evaporated under a reduced pressure
  6. additionAfter adding ethyl acetate the mixture
  7. extractionwas extracted with 15 ml of 1N hydrochloric acid
  8. extractionThe aqueous extract
  9. extractionextracted with total 70 ml of chloroform
  10. extractionThe organic extract
  11. washwas washed with water
  12. dry with materiala saturated sodium chloride aqueous solution, dried over magnesium sulfate
  13. customevaporated under a reduced pressure

Sources & evidence

ORD record
ord-157765f0bf634ec6a3b0307fd16ce9e6
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

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