Ethylenediamine → N-(2-aminoethyl)-2,2,2-trifluoroacetamide

HRID 1735465Notes

Reaction equation

HRID 1735465 reaction equation
C(O[C:4](=[O:9])[C:5]([F:8])([F:7])[F:6])C.[CH2:10]([NH2:13])[CH2:11][NH2:12].C(N(CC)CC)C>CO>[C:5]([C:4]([NH:12][CH2:11][CH2:10][NH2:13])=[O:9])([F:6])([F:7])[F:8]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 8471TriethylamineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 229755N-(2-aminoethyl)-2,2,2-trifluoroacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-1-trifluoroacetylethyldiamine (CF3CONH(CH2)2NH2 is prepared by adding ethyltrifluoroacetate (1.2 ml, 10 mmol) dropwise over one hour to a stirred mixture of ethylenediamine (0.6 g; 10 mmol) and triethylamine (1 ml; 7 mmol) in 20 ml methanol. The solution is stirred overnight. After removal of solvents, the reaction mixture is flash chromatographed on silica using 0-25% methanol in dichloromethane. The fractions containing the desired product are pooled and concentrated to give a colorless product.

Workup

  1. customAfter removal of solvents
  2. customchromatographed on silica using 0-25% methanol in dichloromethane
  3. additionThe fractions containing the desired product
  4. concentrationconcentrated
  5. customto give a colorless product

Sources & evidence

ORD record
ord-5a958693f89c4159981a1c414879050d
Source dataset
uspto-grants-1996_07
Patent number
US05536821

Reaction notes

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