Methylamine → (3,4,4,5,5,5-Hexafluoro-pent-2-enyl)-methyl-amine

HRID 1837255Notes

Reaction equation

HRID 1837255 reaction equation
[CH3:1][NH2:2].[F:3][C:4]([F:15])([F:14])[C:5]([F:13])([F:12])[C:6](F)([F:10])[CH2:7][CH2:8]I>O1CCCC1>[F:10][C:6]([C:5]([F:13])([F:12])[C:4]([F:15])([F:14])[F:3])=[CH:7][CH2:8][NH:2][CH3:1]

Participants

4

Reactant 2

HCID 6329Methylamine2×HCID 109697Alkyl iodides, C4-20, gamma-omega-perfluoro

Product 1

HCID 54094144(3,4,4,5,5,5-Hexafluoro-pent-2-enyl)-methyl-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.55 g of methylamine is condensed in a solution of 2.6 ml of 1,1,1,2,2,3,3 heptafluor-5-iodo-pentane in 20 ml of anhydrous tetrahydrofuran at −40° C., and it is stirred overnight at room temperature in a pressurized reactor. After the pressurized reactor was opened at −30° C., it is allowed to come to room temperature to allow excess methylamine to evaporate off. Then, the reaction solution is mixed with diethyl ether, washed with saturated common salt solution, dried on magnesium sulfate and concentrated by evaporation in a vacuum. 1.26 g of (3,4,4,5,5,5-hexafluoro-pent-2-enyl)-methyl-amine is obtained as a crude product.

Workup

  1. customwas opened at −30° C.
  2. customto come to room temperature
  3. customto evaporate off
  4. additionThen, the reaction solution is mixed with diethyl ether
  5. washwashed with saturated common salt solution
  6. customdried on magnesium sulfate
  7. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-7b1e8e7ec1d443bd872fd5c4281b2e31
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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