Diethylamine → N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamine

HRID 2352352Notes

Reaction equation

HRID 2352352 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([F:7])=[C:4]([F:6])[F:5].[CH2:10]([NH:12][CH2:13][CH3:14])[CH3:11]>C(Cl)Cl>[F:5][C:4]([N:12]([CH2:13][CH3:14])[CH2:10][CH3:11])([F:6])[CH:3]([F:7])[C:2]([F:9])([F:8])[F:1]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 8302Hexafluoropropylene

Product 1

HCID 136149N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamineYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hexafluoropropylene (260 g; 1.73 mole) is bubbled into a solution of 287 ml (200 g; 2.74 mole) of diethylamine and 400 mL of methylene chloride over approximately 2 hours, keeping an internal temperature of about 10° with use of an ice bath. The reaction mixture is then stirred at room temperature for 18 hours. Low boiling compounds are removed by distillation at 70-80 mm and the product is distilled at 27°-32° C. and 8-10 mm, producing 238 ml (293 g; 1.31 mole) of N-(1,1,2,3,3,3-hexafluoropropyl)diethylamine.

Workup

  1. customan internal temperature of about 10°
  2. customare removed by distillation at 70-80 mm
  3. distillationthe product is distilled at 27°-32° C.

Sources & evidence

ORD record
ord-b4d5f6bb193440acb632582e709fb89d
Source dataset
uspto-grants-1989_10
Patent number
US04876352

Reaction notes

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