Pyridine → N-(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl)-N',N'-dimethylethylenediamine

HRID 1252047Notes

Reaction equation

HRID 1252047 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].N1C=CC=CC=1.[CH3:13][C:14]([CH2:18][CH2:19][CH:20]=[C:21]([CH3:33])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:32])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])=[CH:15][CH2:16]Br>O1CCOCC1>[CH3:13][C:14]([CH2:18][CH2:19][CH:20]=[C:21]([CH3:33])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:32])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])=[CH:15][CH2:16][NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 66053N,N-DimethylethylenediamineHCID 545679811-Bromo-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene

Product 1

HCID 54469208N-(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl)-N',N'-dimethylethylenediamineYield 33.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4.4 g of N,N-dimethylethylenediamine was dissolved in 40 ml of dioxane. 5 ml of pyridine was added to the solution. 17.6 g of 3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl bromide was added thereto and the mixture was heated under reflux for 2 h and poured in ice-water. After extraction with n-hexane followed by washing with water and concentration, the resulting reaction mixture was treated by alumina column chromatography to obtain 6 g (33%) of the title compound as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. extractionAfter extraction with n-hexane
  4. washby washing with water and concentration
  5. customthe resulting reaction mixture
  6. additionwas treated by alumina column chromatography

Sources & evidence

ORD record
ord-c65a5ae679fe4768a33c965ef565759a
Source dataset
uspto-grants-1988_05
Patent number
US04742058

Reaction notes

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