Acetyl chloride → HCID 178473784, compound

HRID 2287422Notes

Reaction equation

HRID 2287422 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(N(CC)CC)C.[C:32](Cl)(=[O:34])[CH3:33]>C1COCC1.O.C(=O)(O)[O-].[Na+]>[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]([C:32](=[O:34])[CH3:33])[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 6367Acetyl chlorideHCID 8471TriethylamineHCID 178505567HCID 178505567, compound

Product 1

HCID 178473784HCID 178473784, compoundYield 27.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirring solution of 4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1H-imidazol-2-yl]piperidine (0.76 mmol,0.30 g) in THF (5 mL) was added triethylamine (2.7 mmol,0.27 g) and acetyl chloride (0.91 mmol,71.5 mg) and the reaction stirred at room temperature overnight. The reaction was diluted with water (50 mL) and saturated sodium bicarbonate (10 mL) and the aqueous phase 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 5% MeOH:CH2Cl2. The product containing fractions were combined and evaporated to give a yellow oil. This oil was crystallized from diethyl ether to give 75 mg of the title compound as a white powder.

Workup

  1. extractionthe aqueous phase extracted with ethyl acetate (2×50 mL)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. customthe solvent evaporated under reduced pressure
  4. customThe residue was chromatographed over silica
  5. washeluting with 2.5% to 5% MeOH
  6. additionThe product containing fractions
  7. customevaporated
  8. customto give a yellow oil
  9. customThis oil was crystallized from diethyl ether

Sources & evidence

ORD record
ord-f7d5ce2800e64effa39ed9f60c3b3e69
Source dataset
uspto-grants-2000_07
Patent number
US06083949

Reaction notes

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