Hydrochloric Acid → HCID 178479513, compound

HRID 1700529Notes

Reaction equation

HRID 1700529 reaction equation
[C:1]1([CH:7]2[CH2:19][C:18](=O)[C:17]3[C:16]4[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=4[NH:10][C:9]=3[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([NH:24][NH2:25])([NH2:23])=[NH:22].[ClH:26].Cl.O>C(O)C>[ClH:26].[NH:24]([N:25]=[C:18]1[C:17]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[NH:10][C:9]=2[CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:19]1)[C:21]([NH2:23])=[NH:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 18317736HCID 18317736, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178479513HCID 178479513, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-phenyl-1,2,3,4,5,6,7,8-octahydrocarbazol-4-one (0.8 g), aminoguanidine hydrochloride (0.35 g), concentrated hydrochloric acid (0.15 ml), water (0.15 ml) and ethanol (50 ml) was refluxed for 1 hour. Under reduced pressure, the solvent was evaporated, and to the residue was added sodium hydrogen carbonate solution. The solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (EtOAc/MeOH) and dissolved in ethanol. To the solution was added 1N hydrochloric acid (4 ml), and the solvent was evaporated. The residue was recrystallized from ethanol to give 4-guanidinoimino-2-phenyl-1,2,3,4,5,6,7,8-octahydrocarbazole hydrochloride (Compound 5) (0.53 g) as amorphous.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customUnder reduced pressure, the solvent was evaporated
  3. additionto the residue was added sodium hydrogen carbonate solution
  4. extractionThe solution was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customUnder reduced pressure, the solvent was evaporated
  8. customthe residue was purified with silica gel column chromatography (EtOAc/MeOH)
  9. dissolutiondissolved in ethanol
  10. additionTo the solution was added 1N hydrochloric acid (4 ml)
  11. customthe solvent was evaporated
  12. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-b59dbc2558504e3bb409811a60188d3c
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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