Water → HCID 18797212, compound

HRID 1003589Notes

Reaction equation

HRID 1003589 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1.[OH-].[K+].O>C(O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:14]3([OH:17])[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 337214-PiperidoneHCID 871116-Chloroindole

Product 1

HCID 18797212HCID 18797212, compoundYield 7.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.0 gm (13.2 mMol) 6-chloroindole and 4.06 gm (26.3 mMol) 4-piperidinone in 30 mL ethanol which contained 2.21 gm (39.6 mMol) potassium hydroxide was stirred at room temperature for 48 hours. Water (50 mL) was added dropwise to the reaction mixture over 30 minutes. The reaction mixture was allowed stir an additional 2 hours and the solid which formed was collected by filtration to provide a sticky orange solid. A portion of the solid was triturated with acetonitrile and filtered, washed with diethyl ether and dried under reduced pressure to provide 0.254 gm (7.4%) of the title compound as a colorless powder.

Workup

  1. stirringThe reaction mixture was allowed stir an additional 2 hours
  2. customthe solid which formed
  3. filtrationwas collected by filtration
  4. customto provide a sticky orange solid
  5. customA portion of the solid was triturated with acetonitrile
  6. filtrationfiltered
  7. washwashed with diethyl ether
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-d873fc9a9ae2404f965e959a43b89568
Source dataset
uspto-grants-2000_04
Patent number
US06046215

Reaction notes

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