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

HRID 373197

Reaction equation

HRID 373197 reaction equation
[C:1]([O:14]CC)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:17]([NH2:20])[CH2:18][NH2:19]>O1CCCC1>[NH2:19][CH2:18][CH2:17][NH:20][C:1](=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 7800Ethyl Dodecanoate

Product 1

HCID 82394Dodecanamide, N-(2-aminoethyl)-Yield 44.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 23 g of ethyl dodecanoate and 62.7 g of ethylenediamine in 100 ml of tetrahydrofuran (THF) was refluxed for 3 hours and the excess THF was distilled off. The reaction mixture was heated at 100° C. for 16 hours, cooled to room temperature, poured into cold water and extracted with ether. After drying, the organic solution was concentrated to give 15.7 g of crude product and this was recrystallized from ether-hexane to give 10.9 g of pure product, m.p. 64°-66° C.

Workup

  1. distillationthe excess THF was distilled off
  2. temperaturecooled to room temperature
  3. additionpoured into cold water
  4. extractionextracted with ether
  5. customAfter drying
  6. concentrationthe organic solution was concentrated
  7. customto give 15.7 g of crude product
  8. customthis was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-4ba5e978f6544351a643c1f9b3b0d08d
Source dataset
uspto-grants-1992_11
Patent number
US05162315

Linked notes

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