Water → 2,2,2-trifluoro-N-[2-(methylamino)ethyl]acetamide

HRID 2234672Notes

Reaction equation

HRID 2234672 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH2:5].O.[F:7][C:8]([F:15])([F:14])[C:9]([O:11]CC)=O>C(#N)C>[F:15][C:8]([F:7])([F:14])[C:9]([NH:5][CH2:4][CH2:3][NH:2][CH3:1])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 8014N-MethylethylenediamineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 107022842,2,2-trifluoro-N-[2-(methylamino)ethyl]acetamideYield 100.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a round bottom flask was added N-methylethylenediamine (1.9 ml, 21.79 mmol), water (0.43 mL), acetonitrile (33 mL) and ethyl trifluoroacetate (6.5 ml, 54.62 mmol). The mixture was stirred at reflux for 18 hours. The mixture was concentrated in vacuo. Dichloromethane was added to the residue and the solid filtered off to give 3.71 g of crude 2,2,2-trifluoro-N-(2-methylamino-ethyl)-acetamide, which was used in step 2 without further purification. MS: m/z 171.1 (M+H+).

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. additionDichloromethane was added to the residue
  4. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-09c15e93bd0b4a97bed4da596d58e725
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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