Sodium Hydroxide → HCID 19600468, compound

HRID 609742Notes

Reaction equation

HRID 609742 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[CH:24]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25]1.[OH-].[Na+]>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[CH:24]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19600424HCID 19600424, compound

Product 1

HCID 19600468HCID 19600468, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(2,3-dihydropyran-2-yl)-3-(N-methylpyrrolidin-3-yl)-1-benzoylindole (Example 18a, 0.158 g, 0.409 mmol) in methanol (5 mL) was added 2N NaOH (6.8 mmol) and the mixture was heated at reflux for 2 hours. The solution was cooled to room temperature and the solvent was evaporated and the product was extracted with CH2Cl2 (3×). The organic layer was dried and concentrated by reduced pressure and purified by column chromatography [10% NH3 (2M in MeOH) in CH2Cl2 ] to yield the title compound (0.035 g, 30%) as a yellow foam; HRMS-FAB+ for C18H22N2O; calc. MH+ :283.1810; found MH+ :283.1839.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customthe solvent was evaporated
  4. extractionthe product was extracted with CH2Cl2 (3×)
  5. customThe organic layer was dried
  6. concentrationconcentrated by reduced pressure
  7. custompurified by column chromatography [10% NH3 (2M in MeOH) in CH2Cl2 ]

Sources & evidence

ORD record
ord-ee8f04965f8c45fe869b01c48a551bc2
Source dataset
uspto-grants-1999_12
Patent number
US05998438

Reaction notes

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