Potassium Hydroxide → HCID 59831606, compound

HRID 268837Notes

Reaction equation

HRID 268837 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([C:12]1[CH:20]=[C:19]2[C:15]([C:16]([C:21]#[N:22])=[CH:17][NH:18]2)=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-:23].[Na+].[OH-].[K+]>CCO>[CH3:1][NH:2][CH2:3][CH2:4][CH:5]([C:12]1[CH:20]=[C:19]2[C:15]([C:16]([C:21]([NH2:22])=[O:23])=[CH:17][NH:18]2)=[CH:14][CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 16112811HCID 16112811, compound

Product 1

HCID 59831606HCID 59831606, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-(3-Methylamino-1-phenyl-propyl)-1H-indole-3-carbonitrile CLV (170 mg, 0.59 mmol) in EtOH (5 ml) was added 50% aqueous solution of NaOH (5 ml). The mixture was refluxed for 90 minutes and excess KOH was added. The resulting mixture was refluxed for additional 48 hours, cooled to room temperature, and concentrated. The residue was partitioned between H2O and CHCl3, and the aqueous layer was extracted with CHCl3. The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated and purified via flash chromatography (DCM/MeOH/NH4OH) affording 6-(3-Methylamino-1-phenyl-propyl)-1H-indole-3-carboxylic acid amide CLVI as a white powder (59 mg, 33% yield). MS (M+H)=308.

Workup

  1. temperatureThe mixture was refluxed for 90 minutes
  2. temperatureThe resulting mixture was refluxed for additional 48 hours
  3. concentrationconcentrated
  4. customThe residue was partitioned between H2O and CHCl3
  5. extractionthe aqueous layer was extracted with CHCl3
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified via flash chromatography (DCM/MeOH/NH4OH)

Sources & evidence

ORD record
ord-439a64bf41fe4bfa9367b32c50c2aee1
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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