Ethylenediamine → HCID 2767072, compound

HRID 2050790Notes

Reaction equation

HRID 2050790 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].CO[CH:7]1[CH2:11][CH2:10][CH:9](OC)O1.[O:14]1CCO[CH2:16][CH2:15]1>C(O)(=O)C>[C:15]([NH:3][CH2:2][CH2:1][N:4]1[CH:9]=[CH:10][CH:11]=[CH:7]1)(=[O:14])[CH3:16]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 312751,4-DioxaneHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 2767072HCID 2767072, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 140 g of ethylenediamine and 300 g of 2,5-dimethoxytetrahydrofuran in 2000 ml of dioxane and 1700 ml of glacial acetic acid is stirred and refluxed for 6 hours. The reaction mixture is then cooled and the solvents evaporated under reduced pressure at 60°. The dark residue is taken up in methylene chloride and ice and basified with 3N aqueous sodium hydroxide. The organic layer is separated and extracted into 5N aqueous hydrochloric acid. The acid extract is made basic with cooling and is extracted with methylene chloride. The organic phase is dried over magnesium sulfate, treated with 10 g of charcoal and filtered. The methylene chloride is evaporated under reduced pressure to give an N-acetyl-2-(1-pyrrolyl)-ethylamine as an oil.

Workup

  1. temperaturerefluxed for 6 hours
  2. temperatureThe reaction mixture is then cooled
  3. customthe solvents evaporated under reduced pressure at 60°
  4. customThe organic layer is separated
  5. extractionextracted into 5N aqueous hydrochloric acid
  6. extractionThe acid extract
  7. temperaturewith cooling
  8. extractionis extracted with methylene chloride
  9. dry with materialThe organic phase is dried over magnesium sulfate
  10. additiontreated with 10 g of charcoal
  11. filtrationfiltered
  12. customThe methylene chloride is evaporated under reduced pressure

Sources & evidence

ORD record
ord-d3bb379fb47546f8b6fb07c166909b76
Source dataset
uspto-grants-1991_05
Patent number
US05015645

Reaction notes

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