Hydrochloric Acid → 5-(2-Phenylethyl)-1H-indole

HRID 1720069Notes

Reaction equation

HRID 1720069 reaction equation
C(OC([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]=2)[NH:8][CH:7]=1)=O)C.[OH-].[K+].Cl>CCO>[CH2:15]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22419955HCID 22419955, compound

Product 1

HCID 132451555-(2-Phenylethyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the 3-ethyloxycarbonyl-5-phenethylindole (0.4 g, 1.5 mmol) in EtOH 95% (10 ml) was added an excess of KOH (0.5 g) and the reaction mixture was heated at reflux for 2 h. The solution was acidified with 1N HCl (10 ml) and the precipitated material was collected by filtration. The solid was washed well with H2O (2×10 ml) to give the corresponding acid. The acid (0.3 g, 1.2 mmol) was immersed in an oil bath and then heated at about 235°-240° C. for 15 min to give a brown syrup. Distillation of the oil under high vacuum provided 5-phenethylindole.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. filtrationthe precipitated material was collected by filtration
  4. washThe solid was washed well with H2O (2×10 ml)
  5. customto give the corresponding acid
  6. temperatureheated at about 235°-240° C. for 15 min
  7. customto give a brown syrup
  8. distillationDistillation of the oil under high vacuum

Sources & evidence

ORD record
ord-e2f155c7302741edac24e313280b1488
Source dataset
uspto-grants-1996_04
Patent number
US05504101

Reaction notes

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