Potassium Carbonate → HCID 21097257, compound

HRID 2109234Notes

Reaction equation

HRID 2109234 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I.[CH3:15][NH:16][C:17](=[NH:20])SC.Br[C:22](=[CH:25][O:26]C(C)C)[CH:23]=O.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC#N>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:17]2[N:16]([CH3:15])[C:22]([CH:25]=[O:26])=[CH:23][N:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 759941-BenzylpiperazineHCID 534166342-Bromo-3-isopropoxy-propenalHCID 178485204HCID 178485204, compound

Product 1

HCID 21097257HCID 21097257, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 15 mL of MeCN was added 880 mg (4.99 mmol) of N-benzyl-piperazine and 1.16 g (5.00 mmol) of 1,2-dimethyl-isothiourea hydroiodide. The mixture was heated at reflux overnight. Then, 970 mg (5.02 mmol) of 2-bromo-3-isopropoxy-propenal and 2.07 g (15.0 mmol) of K2CO3, and 250 mg of 18-crown-6 were added and the mixture was heated to reflux overnight. The mixture was cooled, concentrated, and dissolved in EtOAc with a small amount of water to dissolve salts. The aqueous phase was extracted twice with EtOAc, and the combined the organics were washed with water and brine, dried over MgSO4, concentrated, and chromatographed to provide 250 mg of 2-(4-benzyl-piperazin-1-yl)-3-methyl-3H-imidazole-4-carbaldehyde and 2-(4-benzyl-piperazin-1-yl)-1-methyl-1H-imidazole-4-carbaldehyde as a 1:1 mixture of isomers.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperaturethe mixture was heated
  4. temperatureto reflux overnight
  5. temperatureThe mixture was cooled
  6. concentrationconcentrated
  7. dissolutiondissolved in EtOAc with a small amount of water
  8. dissolutionto dissolve salts
  9. extractionThe aqueous phase was extracted twice with EtOAc
  10. washorganics were washed with water and brine
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated
  13. customchromatographed

Sources & evidence

ORD record
ord-f07e268632cb4c3485ec72fa50e4fc39
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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