Potassium Hydroxide → HCID 53877860, compound

HRID 1068214Notes

Reaction equation

HRID 1068214 reaction equation
C([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[N:16]=[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]3[CH:23]=2)[CH2:11][CH2:10]1)(=O)C1C=CC=CC=1.[OH-].[K+]>C(O)C>[N:16]1[C:15]([CH:12]2[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]2)=[CH:23][N:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=12

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21193119HCID 21193119, compound

Product 1

HCID 53877860HCID 53877860, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 70 mg of 1-benzoyl-4-(imidazo[1,2-a]pyridin-2-yl)-piperidine (from Step A) in 4 mL of ethanol was added 1 mL of 45% KOH solution. The reaction was refluxed for 14 hours. After concentration, the mixture was partitioned between EtOAc and water. Aqueous layer was extracted with EtOAc (3×). The combined organic phase was washed with brine, dried over MgSO4 and concentrated to give 22 mg of the title compound as a viscous oil.

Workup

  1. temperatureThe reaction was refluxed for 14 hours
  2. concentrationAfter concentration
  3. customthe mixture was partitioned between EtOAc and water
  4. extractionAqueous layer was extracted with EtOAc (3×)
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c1c6fffea9644984bfbad5733b800a29
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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