Hydrochloric Acid → HCID 14801566, compound

HRID 374373Notes

Reaction equation

HRID 374373 reaction equation
O1CCCC1.[CH2:6]([NH:13][C:14](=O)[C:15]1[C:16](=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl>CO>[CH2:20]([NH:19][CH2:17][C:16]1[C:15]([CH2:14][NH:13][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 3267470HCID 3267470, compound

Product 1

HCID 14801566HCID 14801566, compoundYield 12.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 1M solution of borane-tetrahydrofuran complex (24 ml) was added dropwise under ice cooling a 5 ml tetrahydrofuran solution containing 3.6 g of N,N'-diheptylphthalamide obtained in Example 2 under an argon gas stream, and the mixture was warmed up slowly and then heated under reflux for one hour. After cooling, 2 ml methanol was added dropwise under ice cooling, and the mixture was heated under reflux for 30 minutes. After cooling in ice, 4.24 ml concentrated hydrochloric acid was added, and the mixture was again heated under reflux for 30 minutes. The solvent was distilled off under reduced pressure, and the residue was basified by addition of an aqueous solution of caustic soda and extracted with chloroform. After distilling off the chloroform from the extract, the residue was purified by silica gel column chromatography, giving 0.43 g of N,N'-diheptyl-o-xylylenediamine.

Workup

  1. temperaturethe mixture was warmed up slowly
  2. temperatureheated
  3. temperatureunder reflux for one hour
  4. temperatureAfter cooling
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for 30 minutes
  7. temperatureAfter cooling in ice
  8. temperaturethe mixture was again heated
  9. temperatureunder reflux for 30 minutes
  10. distillationThe solvent was distilled off under reduced pressure
  11. additionthe residue was basified by addition of an aqueous solution of caustic soda
  12. extractionextracted with chloroform
  13. distillationAfter distilling off the chloroform from the extract
  14. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-99b27246e7c346598af3c0d1bf95cf23
Source dataset
uspto-grants-1992_11
Patent number
US05166429

Reaction notes

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