Methanol → HCID 178443596, compound

HRID 1437071Notes

Reaction equation

HRID 1437071 reaction equation
CO.N1CC[CH2:6][CH2:5][CH2:4]1.Cl.Cl.[CH3:11][C:12]1[CH:33]=[CH:32][C:15]([CH2:16][NH:17][C:18]([NH:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[NH:22])=[NH:19])=[CH:14][CH:13]=1>CC(C)=O>[CH2:24]([NH:23][C:21]1[NH:20][C:18]([NH:17][CH2:16][C:15]2[CH:14]=[CH:13][C:12]([CH3:11])=[CH:33][CH:32]=2)=[N:19][C:5]([CH3:6])([CH3:4])[N:22]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 887MethanolHCID 8082PiperidineHCID 178443631HCID 178443631, compound

Product 1

HCID 178443596HCID 178443596, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

40 ml of methanol, 80 ml of acetone and 16 ml (16.2 mmol) of piperidine were added to 3.0 g (7.7 mmol) of N1-(4-methylbenzyl)-N5-octyl-biguanide dihydrochloride, and the mixture was refluxed for 23 hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (elution with a mixture of chloroform, methanol and acetic acid (9:0.5:0.5)). 50 ml of ethanol and 50 ml of water were added to the resulting colorless resinous solid, and the pH of the mixture was adjusted to 11 to 12 with 5N sodium hydroxide. The mixture was refluxed for 1 hour, and the solvent was distilled off under reduced pressure. The residue was washed with water, and dried well under reduced pressure to obtain 1.3 g of a colorless solid.

Workup

  1. temperaturethe mixture was refluxed for 23 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 and acetic acid (9:0.5:0.5))
  6. addition50 ml of ethanol and 50 ml of water were added to the resulting colorless resinous solid
  7. temperatureThe mixture was refluxed for 1 hour
  8. distillationthe solvent was distilled off under reduced pressure
  9. washThe residue was washed with water
  10. customdried well under reduced pressure

Sources & evidence

ORD record
ord-b27484d98df749ec8ca1cfb19d3b7375
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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