Acetyl chloride → HCID 178473802, compound

HRID 2287436Notes

Reaction equation

HRID 2287436 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][C:13]([CH:15]3[CH2:20][CH2:19][CH2:18][NH:17][CH2:16]3)=[N:12][C:11]=2[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:34](Cl)(=[O:36])[CH3:35]>C1COCC1.OS([O-])(=O)=O.[K+]>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][C:13]([CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([C:34](=[O:36])[CH3:35])[CH2:16]3)=[N:12][C:11]=2[C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178478641HCID 178478641, compound

Product 1

HCID 178473802HCID 178473802, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516920Potassium bisulfateSolvent

Procedure

To a stirring solution of 3-[5-(4-fluorophenyl)-4-pyridin-4-yl-1H-imidazol-2-yl]piperidine dihydrochloride (0.76 mmol, 0.3 g) in THF (5.0 mL) was added triethylamine (3.3 mmol, 0.33 g) and acetyl chloride (2.3 mmol, 0.18 g). The reaction was stirred at room temperature for 1H, diluted with 10% KHSO4 (50 mL) and extracted with ethyl acetate (2×50 mL). The organics were combined, washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was chromatographed over silica, eluting with 3% MeOH:CH2Cl2. The pure fractions were collected and evaporated under reduced pressure. The resulting film was evaporated from CH2Cl2 :hexanes to give 0.2 g of the title compound as a white foam.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was chromatographed over silica
  6. washeluting with 3% MeOH
  7. customThe pure fractions were collected
  8. customevaporated under reduced pressure
  9. customThe resulting film was evaporated from CH2Cl2

Sources & evidence

ORD record
ord-a90049b7027b420a879500816858e3ee
Source dataset
uspto-grants-2000_07
Patent number
US06083949

Reaction notes

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