Acrylonitrile → HCID 12403257, compound

HRID 658330Notes

Reaction equation

HRID 658330 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6][CH2:7][CH2:8][NH2:9].[C:17](#[N:20])[CH:18]=[CH2:19]>C(O)(=O)C>[C:17]([CH2:18][CH2:19][N:9]([CH2:8][CH2:7][CH2:6][N:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:4][CH2:3][CH2:2][N:1]([CH2:4][CH2:3][C:2]#[N:1])[CH2:12][CH2:11][C:10]#[N:5])[CH2:6][CH2:7][C:8]#[N:9])#[N:20]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 12403256N~1~-(3-Aminopropyl)-N~1~-benzylpropane-1,3-diamine

Product 1

HCID 12403257HCID 12403257, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.43 g of acetic acid was added to 4.00 g of N,N-bis(3-aminopropyl)benzylamine and 100 mL of acrylonitrile and the mixture was heated under reflux for 14 hours. After the reaction mixture was concentrated, 150 mL of water was added thereto and the mixture was neutralized by 4.60 g of 28% ammonia water, followed by extraction of the mixture with ethyl acetate (150 mL). After the organic layer was washed with water, it was dried with anhydrous magnesium sulfate. The solvent was distilled off to give 6.59 g of the title compound as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 14 hours
  3. concentrationAfter the reaction mixture was concentrated
  4. addition150 mL of water was added
  5. extractionfollowed by extraction of the mixture with ethyl acetate (150 mL)
  6. washAfter the organic layer was washed with water, it
  7. dry with materialwas dried with anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-da41874951894136a0c41df125b26942
Source dataset
uspto-grants-2011_12
Patent number
US08076478B2

Reaction notes

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