Potassium Carbonate → HCID 25103657, compound

HRID 1675327Notes

Reaction equation

HRID 1675327 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1>CS(C)=O>[CH3:33][N:30]1[CH2:31][CH2:32][CH:27]([O:1][C:2]2[CH:3]=[C:4]([S:8]([N:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=[CH:12]3)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=2)[CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 793424-chloro-N-methylpiperidineHCID 59272903HCID 59272903, compound

Product 1

HCID 25103657HCID 25103657, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
42.5 °C

Procedure

1-(3′-Hydroxybenzenesulfonyl) indole, (0.36 mmol, 0.1 grams) (obtained from preparation 1), was dissolved in dimethyl sulfoxide (2 mL). Potassium carbonate (0.074 grams) was added and the resulting reaction mixture was stirred 40-45° C. for a period of one hour. In another round bottom flask, 4-chloro-N-methylpiperidine (0.54 mmol, 0.072 grams) was dissolved in dimethyl sulfoxide (1.5 mL). The content of the first flask were added to the second flask at 40-45° C. The resulting reaction mass was further heated to 140-145° C. and maintained there for a period of 5 hours while monitoring the reaction by thin layer chromatography. Cooled the reaction mass to room temperature, poured it onto water (25 mL) and extracted the product with ethyl acetate (30 mL×3). Combined organic extracts were dried over sodium sulfate and the volatiles were removed under the reduced pressure to obtain 0.110 grams crude compound. The compound was purified by column chromatography using silica gel (100-200 mesh), eluent being ethyl acetate and 1% triethylamine to obtain 50 mg of pure compound.

Workup

  1. customthe resulting reaction mixture
  2. additionThe content of the first flask were added to the second flask at 40-45° C
  3. customThe resulting reaction mass
  4. temperaturewas further heated to 140-145° C.
  5. temperaturemaintained there for a period of 5 hours
  6. customthe reaction by thin layer chromatography
  7. temperatureCooled the reaction mass to room temperature
  8. additionpoured it onto water (25 mL)
  9. extractionextracted the product with ethyl acetate (30 mL×3)
  10. dry with materialCombined organic extracts were dried over sodium sulfate
  11. customthe volatiles were removed under the reduced pressure
  12. customto obtain 0.110 grams crude compound
  13. customThe compound was purified by column chromatography

Sources & evidence

ORD record
ord-fadb2b86b1134600860236c593ada2bf
Source dataset
uspto-grants-2011_08
Patent number
US08003670B2

Reaction notes

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