HCID 18797421, compound → HCID 18797135, compound

HRID 1003586Notes

Reaction equation

HRID 1003586 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:19]2[CH2:20][CH2:21][N:22]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:23][CH:24]=2)(=O)=O)C=CC=CC=1>C(O)C>[CH2:25]([N:22]1[CH2:23][CH:24]=[C:19]([C:11]2[NH:10][C:18]3[C:13]([CH:12]=2)=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:20][CH2:21]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 1

HCID 18797421HCID 18797421, compound

Product 1

HCID 18797135HCID 18797135, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.05 gm (2.5 mMol) 1-phenylsulfonyl-2-(1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in 60 mL ethanol containing 15 mL 2N sodium hydroxide was heated at reflux for 18 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and 2N sodium hydroxide. The phases were separated and the organic phase was washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane containing 2% methanol. Fractions shown to contain product were combined and concentrated under reduced pressure to provide 0.521 gm (74%) of the desired compound as a light tan solid.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and 2N sodium hydroxide
  4. customThe phases were separated
  5. washthe organic phase was washed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluting with dichloromethane containing 2% methanol
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-68b9271e5ff642eb9520e8f8dc862ffb
Source dataset
uspto-grants-2000_04
Patent number
US06046215

Reaction notes

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