1-Iodooctadecane → N-octadecyl-N-pyridin-2-ylpyridin-2-amine

HRID 495249

Reaction equation

HRID 495249 reaction equation
[CH:1]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]=[CH:3][CH:2]=1.[OH-].[K+].I[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CN(C)C=O>[CH2:34]([N:7]([C:5]1[CH:6]=[CH:1][CH:2]=[CH:3][N:4]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][N:13]=1)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17]

Participants

5

Reactant 3

HCID 124021-IodooctadecaneHCID 145472,2'-DipyridylamineHCID 14797Potassium Hydroxide

Product 1

HCID 66627706N-octadecyl-N-pyridin-2-ylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 1.0 g 2,2′-dipyridylamine, 1.0 g of pulverized potassium hydroxide and 15 ml of N,N-dimethylformamide. After stirring for 1 hour under nitrogen, the mixture was cooled to 5 C and 2.2 g of 1-iodooctadecane were added. The mixture was allowed to warm to 22 C and stirred for 16 hours, then heated to 40 C for 2 hours. After quenching with 25 ml water and cooling to 22 C, the product was filtered and washed with water. The product was dissolved in 25 ml hot ethanol with 100 mg activated carbon, stirred for 30 minutes and filtered through celite. After adding 25 ml water and cooling to 5 C, the product was filtered, washed with water and dried leaving 2.1 g light yellow solid.

Workup

  1. additionwere added
  2. temperatureto warm to 22 C
  3. stirringstirred for 16 hours
  4. temperatureheated to 40 C for 2 hours
  5. customAfter quenching with 25 ml water
  6. temperaturecooling to 22 C
  7. filtrationthe product was filtered
  8. washwashed with water
  9. dissolutionThe product was dissolved in 25 ml hot ethanol with 100 mg
  10. stirringstirred for 30 minutes
  11. filtrationfiltered through celite
  12. additionAfter adding 25 ml water
  13. temperaturecooling to 5 C
  14. filtrationthe product was filtered
  15. washwashed with water
  16. customdried
  17. customleaving 2.1 g light yellow solid

Sources & evidence

ORD record
ord-9a1d73b8a7ca4f36b2885474a8a54016
Source dataset
uspto-grants-2009_05
Patent number
US07538931B2

Linked notes

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