Potassium Hydroxide → HCID 19600470, compound

HRID 609743Notes

Reaction equation

HRID 609743 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH:2]1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12](C(=O)C1C=CC=CC=1)[CH:11]=[C:10]2[CH2:24][CH2:25][N:26]([CH3:28])[CH3:27].[OH-].[K+]>CO>[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH:2]1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:24][CH2:25][N:26]([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 19600464HCID 19600464, compound

Product 1

HCID 19600470HCID 19600470, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 5-(2,3-dihydropyran-2-yl)-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole (Example 18e, 0.048, 0.129 mmol) was added a 5% solution of KOH in MeOH (5 mL) followed by methanol (5 mL). The solution was heated at reflux for 3 hours. At this time, the solution was allowed to cool, and was filtered and concentrated by reduced pressure. The crude product was purified by column chromatography [7% NH3 (2M in MeOH) in CH2Cl2 ] to yield the title compound as a yellow oil (19.6 mg, 56%); HRMS-FAB+ for C17H22N2O: calc. MH+ :271.1810; found MH+ :271.1826.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 hours
  3. temperatureto cool
  4. filtrationwas filtered
  5. concentrationconcentrated by reduced pressure
  6. customThe crude product was purified by column chromatography [7% NH3 (2M in MeOH) in CH2Cl2 ]

Sources & evidence

ORD record
ord-9e0630313acf47de80f193bed7af3016
Source dataset
uspto-grants-1999_12
Patent number
US05998438

Reaction notes

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