Benzyl Chloride → HCID 178505569, compound

HRID 2287425Notes

Reaction equation

HRID 2287425 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:10][C:9]=2[C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[CH2:30](Cl)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(#N)C.CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([CH:13]3[CH2:14][CH2:15][N:16]([CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:17][CH2:18]3)=[N:10][C:9]=2[C:19]2[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 7503Benzyl ChlorideHCID 516892Sodium BicarbonateHCID 178505567HCID 178505567, compound

Product 1

HCID 178505569HCID 178505569, compoundYield 35.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirring solution of 4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1H-imidazol-2-yl]piperidine (0.51 mmol, 0.20 g) in acetonitrile (4.0 mL) and methanol (2.0 mL) was added sodium bicarbonate (1.8 mmol, 0.15 g) and benzyl chloride (0.51 mmol, 64.0 mg). The reaction was heated to reflux overnight, cooled, diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over anhydrous sodium sulfate and the solvent evaporated under reduced pressure. The residue was chromatographed over silica, eluting with 2.5% to 10% MeOH:CH2Cl2. The product containing fractions were evaporated under reduce pressure and crystallized from diethyl ether to give 74 mg of the title compound as a white powder.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. temperaturecooled
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. customthe solvent evaporated under reduced pressure
  7. customThe residue was chromatographed over silica
  8. washeluting with 2.5% to 10% MeOH
  9. additionThe product containing fractions
  10. customwere evaporated
  11. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-76dcd4f0af8d448fabc941f8b3761f07
Source dataset
uspto-grants-2000_07
Patent number
US06083949

Reaction notes

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