Methanol → HCID 178443387, compound

HRID 1437089Notes

Reaction equation

HRID 1437089 reaction equation
CO.N1CC[CH2:6][CH2:5][CH2:4]1.[ClH:9].Cl.C[O:12][C:13]([C:15]1[CH:38]=[CH:37][C:18]([CH2:19][NH:20][C:21]([NH:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[NH:25])=[NH:22])=[CH:17][CH:16]=1)=[O:14]>CC(C)=O>[ClH:9].[CH3:4][C:5]1([CH3:6])[N:22]=[C:21]([NH:20][CH2:19][C:18]2[CH:37]=[CH:38][C:15]([C:13]([OH:12])=[O:14])=[CH:16][CH:17]=2)[NH:23][C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[N:25]1

Participants

5

Reactant 3

HCID 887MethanolHCID 8082PiperidineHCID 178443403HCID 178443403, compound

Product 1

HCID 178443387HCID 178443387, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

50 ml of methanol, 100 ml of acetone and 1.6 ml of piperidine were added to 5.0 g (10.8 mmol) of N1-(4-methoxycarbonylbenzyl)-N5-decyl-biguanide dihydrochloride. The mixture was refluxed for 24 hours, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (elution with a mixture of chloroform/methanol/acetic acid (8:0.7:0.7→8:1:1)). 4.0 g of the purified product was dissolved in 60 ml of ethanol, and to the solution were added 60 ml of water and 2.4 ml of 5N aqueous sodium hydroxide. The mixture was refluxed for 2 hours, and 5 ml of concentrated hydrochloric acid was added thereto. The mixture was concentrated under reduced pressure, and extracted with chloroform. The aqueous layer was separated, and the solvent was distilled off under reduced pressure. The residue was dried well under reduced pressure, heated and extracted with methanol. The extract was filtered, and cooled. The resulting precipitates were filtered, and the solvent of the filtrate was distilled off under reduced pressure. The residue was extracted with ethanol under heating, and filtered. The solvent of the filtrate was distilled off under reduced pressure, and ether was added to the residue to obtain 3.4 g of a white yellow solid.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (
  4. washelution
  5. additionwith a mixture of chloroform/methanol/acetic acid (8:0.7:0.7→8:1:1))
  6. dissolution4.0 g of the purified product was dissolved in 60 ml of ethanol
  7. additionto the solution were added 60 ml of water and 2.4 ml of 5N aqueous sodium hydroxide
  8. temperatureThe mixture was refluxed for 2 hours
  9. addition5 ml of concentrated hydrochloric acid was added
  10. concentrationThe mixture was concentrated under reduced pressure
  11. extractionextracted with chloroform
  12. customThe aqueous layer was separated
  13. distillationthe solvent was distilled off under reduced pressure
  14. customThe residue was dried well under reduced pressure
  15. temperatureheated
  16. extractionextracted with methanol
  17. filtrationThe extract was filtered
  18. temperaturecooled
  19. customThe resulting precipitates
  20. filtrationwere filtered
  21. distillationthe solvent of the filtrate was distilled off under reduced pressure
  22. extractionThe residue was extracted with ethanol
  23. temperatureunder heating
  24. filtrationfiltered
  25. distillationThe solvent of the filtrate was distilled off under reduced pressure, and ether
  26. additionwas added to the residue

Sources & evidence

ORD record
ord-71c83912e32a4c35835f4216bcce2c1e
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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