Ammonium Hydroxide → HCID 178525122, compound

HRID 2287428Notes

Reaction equation

HRID 2287428 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:19]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH:35]=O)[CH2:31][CH2:30]1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])(=O)C.[NH4+:41].[OH-].[NH4+:43]>C(O)(=O)C>[CH2:19]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([C:35]2[NH:41][C:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)=[C:10]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[N:43]=2)[CH2:31][CH2:30]1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 2776272Benzyl 4-formylpiperidine-1-carboxylateHCID 154548601-(3,4-Dichlorophenyl)-2-pyridin-4-yl-ethane-1,2-dione

Product 1

HCID 178525122HCID 178525122, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(3,4-Dichlorophenyl)-2-pyridin-4-yl-ethane-1,2-dione (2.8 g, 10 mmol), 4-formylpiperidine-1-carboxylic acid benzyl ester (2.47 g, 10 mmol) and ammonium acetate (7.7 g, 100 mmol) were dissolved in acetic acid (65 mL) and heated to reflux for 2.5 hour and allowed to cool to ambient temperature. The reaction mixture was then poured over an ammonium hydroxide (100 mL) and ice mixture. This aqueous layer was extracted with ethyl acetate (3×200 mL) and the organic layers were combined, washed with brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated at reduced pressure. The resulting oil was chromatographed on silica gel eluting with 97:3 dichloromethane:methanol to give the imidazole as a foam (2.3 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2.5 hour
  3. extractionThis aqueous layer was extracted with ethyl acetate (3×200 mL)
  4. washwashed with brine (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customThe resulting oil was chromatographed on silica gel eluting with 97:3 dichloromethane

Sources & evidence

ORD record
ord-9e0f9496d146482c8bcf1ead5a032c9b
Source dataset
uspto-grants-2000_07
Patent number
US06083949

Reaction notes

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