Acetone → HCID 178476233, compound

HRID 1437072Notes

Reaction equation

HRID 1437072 reaction equation
[OH-].[Na+].Cl.Cl.[CH3:5][O:6][C:7]1[CH:30]=[CH:29][C:10]([CH2:11][NH:12][C:13]([NH:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[NH:17])=[NH:14])=[CH:9][CH:8]=1.[CH3:31][C:32]([CH3:34])=[O:33].N1CCCCC1>CO>[C:7]([OH:6])(=[O:33])[CH3:30].[CH3:31][C:32]1([CH3:34])[N:14]=[C:13]([NH:12][CH2:11][C:10]2[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:30][CH:29]=2)[NH:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[N:17]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 8082PiperidineHCID 14798Sodium HydroxideHCID 178443406HCID 178443406, compound

Product 1

HCID 178476233HCID 178476233, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

55 ml of 5N aqueous sodium hydroxide was added to 40 g (92.1 mmol) of N1-(4-methoxybenzyl)-N5-decylbiguanide dihydrochloride in 400 ml of methanol, and the mixture was stirred at 60° C. for 30 minutes. The solvent was distilled off under reduced pressure, and the residue was extracted with chloroform. The extract was washed with water, and the solvent was distilled off under reduced pressure to give a residue, to which were added 450 ml of acetone, 150 ml of methanol and 6.4 ml (46.6 mmol) of piperidine. The mixture was refluxed for 15 hours, and the solvent was distilled off under reduced pressure. The residue was washed with water while stirring, dissolved in ethyl acetate, and washed with water. After removal of the solvent by evaporation under reduced pressure, the residue was dried under reduced pressure to obtain 37 g of a colorless solid (1). Then, 2.3 g (5.9 mmol) of the solid was dissolved in 100 ml of methanol, and 169 g (19.7 mmol) of methanesulfonic acid was added thereto. The solvent was distilled off under reduced pressure, and the residue was dissolved in 70% aqueous acetonitrile. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (elution with a mixture of chloroform and methanol (9:1.5)). Crystallization took place upon addition of ether to obtain 1.9 g of colorless crystals (2) having a melting point of 56 to 58° C.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. extractionthe residue was extracted with chloroform
  3. washThe extract was washed with water
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto give a residue
  6. temperatureThe mixture was refluxed for 15 hours
  7. distillationthe solvent was distilled off under reduced pressure
  8. washThe residue was washed with water
  9. stirringwhile stirring
  10. dissolutiondissolved in ethyl acetate
  11. washwashed with water
  12. customAfter removal of the solvent
  13. customby evaporation under reduced pressure
  14. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-192d06b373234c75babd4944e0768bbd
Source dataset
uspto-grants-2009_11
Patent number
US07622469B2

Reaction notes

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