Hydrochloric Acid → HCID 178479511, compound

HRID 1700534Notes

Reaction equation

HRID 1700534 reaction equation
[CH2:1]([N:8]1[C:16]2[CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][C:12](=O)[C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([NH:27][NH2:28])([NH2:26])=[NH:25].[ClH:29].Cl.O>C(O)C>[ClH:29].[CH2:1]([N:8]1[C:16]2[CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][C:12](=[N:28][NH:27][C:24]([NH2:26])=[NH:25])[C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 18317750HCID 18317750, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178479511HCID 178479511, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-benzyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one (0.8 g), aminoguanidine hydrochloride (0.32 g), concentrated hydrochloric acid (0.13 ml), water (0.13 ml) and ethanol (50 ml) was refluxed for 30 minutes. Under reduced pressure, the solvent was evaporated, and the residue was washed with water and dissolved in ethanol. To the solution was added a solution of 4N hydrochloric acid-ethyl acetate (1 ml), and the mixture was concentrated. The residue was recrystallized from ethanol to give 1-benzyl-4-guanidinoimino-6-phenyl-4,5,6,7-tetrahydroindole hydrochloride (Compound 10) (0.67 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. customUnder reduced pressure, the solvent was evaporated
  3. washthe residue was washed with water
  4. dissolutiondissolved in ethanol
  5. additionTo the solution was added a solution of 4N hydrochloric acid-ethyl acetate (1 ml)
  6. concentrationthe mixture was concentrated
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-efca1aeeaa8741d4ad6f94d2f2185099
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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