Potassium Carbonate → HCID 86747102, compound

HRID 2254398Notes

Reaction equation

HRID 2254398 reaction equation
Cl.[CH3:2][NH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=1.Br[CH2:21][CH:22]=[CH:23][C:24]#[C:25][C:26]([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:27][C:26]([CH3:29])([CH3:28])[C:25]#[C:24]/[CH:23]=[CH:22]\[CH2:21][N:3]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 19744711HCID 19744711, compoundHCID 454895941-Bromo-6,6-dimethylhept-2-en-4-yne

Product 1

HCID 86747102HCID 86747102, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-methyl-3-benzoylaminobenzylamine hydrochloride (277 mg) was dissolved in 3 ml of dimethylformamide, and 221 mg of 1-bromo-6,6-dimethyl-2-hepten-4-yne and 552 mg of potassium carbonate were stirred overnight at room temperature. The reaction mixture was diluted with water, and extracted with ethyl ether. The extract was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The desiccant was separated by filtration, and then the solvent was evaporated. The residue was purified by preparative thin-layer chromatography [thin-layer plate: Kieselgel 60F254, Art. 5744 (a product of E. Merck Co.); developing solvent: hexane/ethyl acetate=3/1] to give the following compounds as colorless oils.

Workup

  1. extractionextracted with ethyl ether
  2. washThe extract was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe desiccant was separated by filtration
  5. customthe solvent was evaporated
  6. customThe residue was purified by preparative thin-layer chromatography [thin-layer plate

Sources & evidence

ORD record
ord-8676d9e8413a433db2e6584af79ef238
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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