Pyridine → HCID 19710734, compound

HRID 843887Notes

Reaction equation

HRID 843887 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16]N)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CC=[CH:20][CH:19]=1.O=[C:25]1[CH2:30][CH2:29][CH:28]([C:31]([O:33]CC)=[O:32])[CH2:27][CH2:26]1>C(O)C>[CH2:19]([CH:26]1[C:25]2[NH:16][C:13]3[C:12](=[CH:11][C:10]([O:9][CH2:2][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)=[CH:15][CH:14]=3)[C:30]=2[CH2:29][CH:28]([C:31]([OH:33])=[O:32])[CH2:27]1)[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochloride

Product 1

HCID 19710734HCID 19710734, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 3.242 gm (12.93 mMol) 4-benzyloxy-phenylhydrazine hydrochloride in 80 mL ethanol were added 1.05 mL (12.93 mMol) pyridine. The resulting mixture was heated to 50° C. for about 20 minutes and then 1.87 mL (11.75 mMol) ethyl 4-oxocyclohexanecarboxylate were added. The resulting mixture was stirred at reflux for 18 hours. The reaction mixture was then concentrated under reduced pressure and the residue partitioned between water and ethyl acetate. The organic phase was separated, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 35% ethyl acetate in hexane. Fractions containing product were combined and concentrated under reduced pressure to give 3.38 gm (83%) of the desired compound.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customthe residue partitioned between water and ethyl acetate
  4. customThe organic phase was separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluting with 35% ethyl acetate in hexane
  9. additionFractions containing product
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-33d314bce17c4c5783618cf8c17a543a
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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