Acetonitrile → 2-[2-(Dimethylamino)ethylamino]succinic acid bis(3,3,4,4,5,5,6,6,6-nonafluorohexyl) ester

HRID 352715Notes

Reaction equation

HRID 352715 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])[CH2:2][CH2:3][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][CH3:45])NC.C(=O)([O-])[O-].[K+].[K+].[C:52](OCC)(=O)C.[C:58](#[N:60])C>>[CH3:52][N:60]([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])[CH3:58]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 57041336N,N-DimethylaminoethylamineHCID 58090242Bis(3,3,4,4,5,5,6,6,6-nonafluorohexyl) butanedioate

Product 1

HCID 226306862-[2-(Dimethylamino)ethylamino]succinic acid bis(3,3,4,4,5,5,6,6,6-nonafluorohexyl) esterYield 54%

Procedure

In an amount of 12.0 g (20 mmol) of 1,4-di(3,3,4,4,5,5,6,6,6-nonafluorohexyl) succinate, 1.9 g (22 mmol) of N,N-dimethylaminoethylamine and 2.9 g (22 mmol) of potassium carbonate were dissolved in 50 mL of acetonitrile and refluxed for 6 hours with heating. Then, the reaction mixture was transferred to a separatory funnel and added with 500 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 to 100:6 (volume ratio)) to obtain 10.7 g (yield: 54%) of the target 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 to 100:6 (volume ratio))

Sources & evidence

ORD record
ord-c9891239e500489c9e8de646ea618b02
Source dataset
uspto-grants-2004_06
Patent number
US06747169B2

Reaction notes

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