N-(2-Hydroxyethyl)ethylenediamine → HCID 86585342, compound

HRID 1168113Notes

Reaction equation

HRID 1168113 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][OH:7].[C:8]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:11])[CH:9]=[CH2:10]>>[CH2:13]([O:12][C:8]([CH2:9][CH2:10][CH:5]([NH:4][CH2:3][CH2:2][NH2:1])[CH2:6][OH:7])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 75617Benzyl acrylate

Product 1

HCID 86585342HCID 86585342, compound

Procedure

A solution of 2-(2-aminoethylamino) ethanol (4.6648 g; 44.8 mmole) dissolved in 35 mL of benzyl acrylate was heated at reflux for 24 hours. The excess reagent was removed under reduced pressure and the resulting oil was purified by flash chromatography using a mixture of dichloromethane and ethyl acetate (60:40) to elute the desired material. Fractions were collected and analyzed to determine which of these contain the product. Solvents were eliminated under vacuum to give 5.8 g (21.9%) of N,N,N′-tris[2-(benzyloxycarbonylethyl]-2-(2aminoethylamino) ethanol (8).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. customThe excess reagent was removed under reduced pressure
  4. customthe resulting oil was purified by flash chromatography
  5. additiona mixture of dichloromethane and ethyl acetate (60:40)
  6. washto elute the desired material
  7. customFractions were collected

Sources & evidence

ORD record
ord-9c8d9f12065e414b9bc7f6df61506fcb
Source dataset
uspto-grants-2003_09
Patent number
US06623721B2

Reaction notes

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