Acetonitrile → 1,4-Di(3,3,4,4,5,5,6,6,6-nonafluorohexyl) 2-(3-(n,n-dimethylamino)propylamino)succinate

HRID 352716Notes

Reaction equation

HRID 352716 reaction equation
[C:1]([O:23][CH2:24][CH2:25][C:26]([F:38])([F:37])[C:27]([F:36])([F:35])[C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30])(=[O:22])/[CH:2]=[CH:3]\[C:4]([O:6][CH2:7][CH2:8][C:9]([F:21])([F:20])[C:10]([F:19])([F:18])[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[O:5].CN[N:41]([CH2:44][CH2:45][CH3:46])NC.C(=O)([O-])[O-].[K+].[K+].[C:53](OCC)(=O)C.[C:59](#[N:61])C>>[CH3:53][N:61]([CH2:46][CH2:45][CH2:44][NH:41][CH:2]([CH2:3][C:4]([O:6][CH2:7][CH2:8][C:9]([F:21])([F:20])[C:10]([F:18])([F:19])[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[O:5])[C:1]([O:23][CH2:24][CH2:25][C:26]([F:37])([F:38])[C:27]([F:35])([F:36])[C:28]([F:33])([F:34])[C:29]([F:32])([F:31])[F:30])=[O:22])[CH3:59]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 56982963N,N-dimethylaminopropylamineHCID 867598121,4-Di(3,3,4,4,5,5,6,6,6-nonafluorohexyl) maleate

Product 1

HCID 879988721,4-Di(3,3,4,4,5,5,6,6,6-nonafluorohexyl) 2-(3-(n,n-dimethylamino)propylamino)succinateYield 75%

Procedure

In an amount of 30.0 g (49 mmol) of 1,4-di(3,3,4,4,5,5,6,6,6-nonafluorohexyl) maleate, 6.8 mL (54 mmol) of N,N-dimethylaminopropylamine and 7.5 g (54 mmol) of potassium carbonate were dissolved in 120 mL of acetonitrile and refluxed for 6 hours with heating. Then, the reaction mixture was transferred to a separatory funnel and added with 1000 mL of ethyl acetate. The organic phase was washed with a saturated aqueous sodium hydrogencarbonate solution. Then, the organic layer was collected, and the organic solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:3 (volume ratio)) to obtain 2.64 g (yield: 75%) of the target compound as a brown oily compound.

Workup

  1. temperaturerefluxed for 6 hours
  2. temperaturewith heating
  3. customThen, the reaction mixture was transferred to a separatory funnel
  4. washThe organic phase was washed with a saturated aqueous sodium hydrogencarbonate solution
  5. customThen, the organic layer was collected
  6. customthe organic solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:3 (volume ratio))

Sources & evidence

ORD record
ord-b6c10d57bf72403dabfc5134ff89c13f
Source dataset
uspto-grants-2004_06
Patent number
US06747169B2

Reaction notes

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