Sodium Hydroxide → HCID 11778220, compound

HRID 1252053Notes

Reaction equation

HRID 1252053 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:11]=2)[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+]>C(O)C>[C:19]1([N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]([CH:7]3[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]3)=[CH:11]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 9996016HCID 9996016, compound

Product 1

HCID 11778220HCID 11778220, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(1-acetyl-4-piperidyl)-1-phenylindole (5.0 g) and 2N aqueous sodium hydroxide solution (30 ml) in ethanol (30 ml) was refluxed for 7.5 hours. Then, 2N aqueous sodium hydroxide (30 ml) was further added and the mixture was refluxed for another 5 hours. Ethanol was then distilled off and the oily residue was extracted with a mixture of chloroform and methanol (30:1 V/V). The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography on alumina (500 g) and elution was carried out with a mixture of chloroform and methanol (100:1 to 5:1 V/V). The fractions containing the desired compound were combined and the solvent was distilled off under reduced pressure to give 1-phenyl-3-(4-piperidyl)indole (3.0 g). The following physical data are those of the hydrochloride.

Workup

  1. temperaturewas refluxed for 7.5 hours
  2. temperaturethe mixture was refluxed for another 5 hours
  3. distillationEthanol was then distilled off
  4. extractionthe oily residue was extracted with a mixture of chloroform and methanol (30:1 V/V)
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe residue was subjected to column chromatography on alumina (500 g) and elution
  9. additionwas carried out with a mixture of chloroform and methanol (100:1 to 5:1 V/V)
  10. additionThe fractions containing the desired compound
  11. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-753fa2d85c1e4af098c2ff77d95fca19
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

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