Hydrochloric Acid → HCID 178456185, compound

HRID 1700533Notes

Reaction equation

HRID 1700533 reaction equation
[C:1]1([CH:7]2[CH2:15][C:14]3[N:13]([CH2:16][CH2:17][CH3:18])[CH:12]=[CH:11][C:10]=3[C:9](=O)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]([NH:23][NH2:24])([NH2:22])=[NH:21].[ClH:25].Cl.O>C(O)C>[ClH:25].[NH:23]([N:24]=[C:9]1[CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:15][C:14]2[N:13]([CH2:16][CH2:17][CH3:18])[CH:12]=[CH:11][C:10]1=2)[C:20]([NH2:22])=[NH:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 18317496HCID 18317496, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178456185HCID 178456185, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-phenyl-1-propyl-4,5,6,7-tetrahydroindol-4-one (0.80 g), aminoguanidine hydrochloride (0.46 g), concentrated hydrochloric acid (0.19 ml), water (0.19 ml) and ethanol (50 ml) was refluxed for 30 minutes. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in water and washed with diethylether. To the mixture was added 1N sodium hydroxide solution, and the mixture 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 dissolved in ethanol. To the solution was added a solution of 4N hydrochloric acid in ethyl acetate (2 ml). The solvent was evaporated, and the residue was recrystallized from ethanol to give 4-guanidinoimino-6-phenyl-1-propyl-4,5,6,7-tetrahydroindole hydrochloride (Compound 9) (1.0 g) as colorless crystals of E/Z compounds.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. customUnder reduced pressure, the solvent was evaporated
  3. dissolutionthe residue was dissolved in water
  4. washwashed with diethylether
  5. additionTo the mixture was added 1N sodium hydroxide solution
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried with magnesium sulfate
  9. customUnder reduced pressure, the solvent was evaporated
  10. dissolutionthe residue was dissolved in ethanol
  11. additionTo the solution was added a solution of 4N hydrochloric acid in ethyl acetate (2 ml)
  12. customThe solvent was evaporated
  13. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-0e3a20a971194952862d9abe30e59b1d
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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