Hydrochloric Acid → HCID 178443970, compound

HRID 1437084Notes

Reaction equation

HRID 1437084 reaction equation
CO.[ClH:3].Cl.Cl.[CH2:6]([NH:13][C:14]([NH:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[NH:18])=[NH:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCC(=O)CC>[ClH:3].[CH2:8]([C:7]1([CH2:12][CH3:11])[N:15]=[C:14]([NH:13][CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[N:18]1)[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178443987HCID 178443987, compound

Product 1

HCID 178443970HCID 178443970, compound

Reagents, catalysts & solvents 1

HCID 7288Ethyl ketoneSolvent

Procedure

100 ml of methanol, 150 ml of 3-pentanone, and 0.5 ml of concentrated hydrochloric acid were added to 6.0 g (15.6 mmol) of N1-benzyl-N5-heptyl-biguanide dihydrochloride. The mixture was refluxed for 24 hours, and the solvent was distilled off under reduced pressure. The residue was dissolved in 100 ml of methanol, and to the solution were added 80 ml of water and 5 ml of 5N aqueous sodium hydroxide. The mixture was refluxed for 1.5 hours, concentrated under reduced pressure and extracted with ethyl acetate. The extract was washed with water, and acidified with 6N hydrochloric acid, and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (elution with a mixture of chloroform and methanol (9:1)) to obtain 4.7 g of a pale yellow resinous solid.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in 100 ml of methanol
  4. additionto the solution were added 80 ml of water and 5 ml of 5N aqueous sodium hydroxide
  5. temperatureThe mixture was refluxed for 1.5 hours
  6. concentrationconcentrated under reduced pressure
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with water
  9. concentrationconcentrated under reduced pressure
  10. customto remove the solvent
  11. customThe residue was purified by silica gel column chromatography (
  12. washelution
  13. additionwith a mixture of chloroform and methanol (9:1))

Sources & evidence

ORD record
ord-968796690deb482686190cde222b8607
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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