Potassium Carbonate → HCID 18941131, compound

HRID 356121Notes

Reaction equation

HRID 356121 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][C:8]2[S:9][C:10]3[CH2:19][C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[C:11]=3[N:12]=2)[CH2:2]1.[C:20](=O)([O-])[O-].[K+].[K+].[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30]>C(O)=O.C=O.O.C(Cl)(Cl)Cl.C(#N)C>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30].[CH3:20][N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][C:8]2[S:9][C:10]3[CH2:19][C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[C:11]=3[N:12]=2)[CH2:2]1

Participants

9

Reactant 3

HCID 11430Potassium CarbonateHCID 444972Fumaric AcidHCID 18941009HCID 18941009, compound

Product 1

HCID 18941131HCID 18941131, compound

Reagents, catalysts & solvents 5

HCID 284Formic AcidSolventHCID 712FormaldehydeSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

In 0.13 ml of formic acid and 0.3 ml of a 35% aqueous formaldehyde solution, 94 mg of 2-(3-piperidylmethyl)-8H-indeno[1,2-d]thiazole was dissolved, followed by heating at 90° C. for 14 hours. The reaction mixture was diluted with water and chloroform, followed by the addition of potassium carbonate to adjust the pH of the aqueous layer to about 8. An organic layer was separated, and the resulting aqueous layer was extracted twice with chloroform. The organic layers were combined and washed with a saturated aqueous solution of sodium chloride. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform-methanol), whereby 99 mg of a brawn oily substance was obtained. The substance was dissolved in 1 ml of acetonitrile, and 40 mg of fumaric acid was added thereto. The resulting mixture was stirred at room temperature for 30 minutes and the crystals formed were collected by filtration, whereby 90 mg of 2-[(1-methyl-3-piperidyl)methyl]-8H-indeno[1,2-d]thiazole fumarate was obtained.

Workup

  1. customAn organic layer was separated
  2. extractionthe resulting aqueous layer was extracted twice with chloroform
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform-methanol), whereby 99 mg of a brawn oily substance
  7. customwas obtained
  8. customthe crystals formed
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-400f04e3f9be41a78f86566f8074e487
Source dataset
uspto-grants-1998_11
Patent number
US05834499

Reaction notes

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