Potassium Hydroxide → HCID 22851257, compound

HRID 233796Notes

Reaction equation

HRID 233796 reaction equation
C([N:9]1[C:17]2[CH:16]=[CH:15][C:14]([I:18])=[C:13]3[CH2:19][C@H:20]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH2:21][C@@H:11]([C:12]=23)[CH2:10]1)(=O)C1C=CC=CC=1.[OH-].[K+]>O>[I:18][C:14]1[CH:15]=[CH:16][C:17]2[NH:9][CH2:10][C@H:11]3[CH2:21][C@@H:20]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH2:19][C:13]=1[C:12]=23

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18652842(2aS,4R)-1-benzoyl-6-iodo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole

Product 1

HCID 22851257HCID 22851257, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 100 g (0.21 mol) of (2aS,4R)-1-benzoyl-6-iodo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole and 1 liter of 1M ethanolic potassium hydroxide was refluxed under nitrogen for 5 hours. The cooled mixture was diluted with two volumes of water, and the product was extracted into methylene chloride. After drying the extract over sodium sulfate the solvent was evaporated leaving 78 g of the debenzoylated product as a light brown oil.

Workup

  1. temperaturewas refluxed under nitrogen for 5 hours
  2. extractionthe product was extracted into methylene chloride
  3. customAfter drying the
  4. extractionextract over sodium sulfate the solvent
  5. customwas evaporated

Sources & evidence

ORD record
ord-5bf0cf2f079e4f39bd52e488d20ed0ca
Source dataset
uspto-grants-1997_01
Patent number
US05594019

Reaction notes

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