N,N-Dimethyl-1,3-propanediamine → HCID 58901133, compound

HRID 548533Notes

Reaction equation

HRID 548533 reaction equation
[F:1][C:2]([C:14]([F:17])([F:16])[F:15])([C:10]([F:13])([F:12])[F:11])[CH2:3][CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[CH3:18][N:19]([CH3:24])[CH2:20][CH2:21][CH2:22][NH2:23]>C(Cl)(Cl)Cl>[CH3:18][N:19]([CH3:24])[CH2:20][CH2:21][CH2:22][NH:23][S:6]([CH2:5][CH2:4][CH2:3][C:2]([F:1])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 58918806HCID 58918806, compound

Product 1

HCID 58901133HCID 58901133, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The 4,5,5,5-tetrafluoro-4-trifluoromethyl-pentanesulfonyl chloride (7.1 grams) can be dissolved in 40 mL of chloroform and added to a solution of 8.6 mL of 3-dimethylaminopropylamine in 40 mL of chloroform at 0° C.-5° C. drop-wise over 45 minutes (Tmax=5° C.) to form a mixture. The mixture can be washed successively with saturated bicarbonate solution (80 mL), water (80 mL), and brine (80 mL). The organic layer can be separated, dried over magnesium sulfate, filtered, and concentrated under vacuum to afford 8 grams (93%) of 4,5,5,5-tetrafluoro-4-trifluoromethyl-pentane-1-sulfonic acid (3-dimethylamino-propyl)-amide by NMR and LC/MS analysis.

Workup

  1. customto form a mixture
  2. washThe mixture can be washed successively with saturated bicarbonate solution (80 mL), water (80 mL), and brine (80 mL)
  3. customThe organic layer can be separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d17f5318329f4aae86a499dda7e4a83d
Source dataset
uspto-grants-2011_05
Patent number
US07943567B2

Reaction notes

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