Potassium Hydroxide → HCID 22851257, compound

HRID 1377816Notes

Reaction equation

HRID 1377816 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-aaac45ef69e148c7a1d0ed41a00f651e
Source dataset
uspto-grants-1997_09
Patent number
US05665758

Reaction notes

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