Sodium Hydroxide → HCID 23118274, compound

HRID 1987763Notes

Reaction equation

HRID 1987763 reaction equation
C([N:4]1[CH2:9][CH2:8][C:7]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[CH:20][N:19]=[CH:18]3)=[CH:13][CH:12]=2)(O)[CH2:6][CH2:5]1)(=O)C.[OH-].[Na+]>Cl>[N:17]1([C:14]2[CH:13]=[CH:12][C:11]([C:7]3[CH2:8][CH2:9][NH:4][CH2:5][CH:6]=3)=[CH:16][CH:15]=2)[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23118279HCID 23118279, compound

Product 1

HCID 23118274HCID 23118274, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 2.5 g of 1-acetyl-4-(4-imidazol-1-ylphenyl)-4-hydroxypiperidine, 30 ml of concentrated hydrochloric acid was added, followed by heating at reflux for 4 hours. After the completion of the reaction, the reaction solution was cooled, neutralized with an aqueous 1N sodium hydroxide solution and then extracted with chloroform. The organic layer was washed with saturated saline and then dried over dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration and concentrating under reduced pressure, the resulting crystal was washed with hexane and then dried to obtain 1.5 g of the objective 4-(4-imidazol-1-ylphenyl)-1,2,3,6-tetrahydropyridine (mp: 150-153° C.).

Workup

  1. temperatureby heating
  2. temperatureat reflux for 4 hours
  3. customAfter the completion of the reaction
  4. temperaturethe reaction solution was cooled
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with saturated saline
  7. customdried
  8. dry with materialover dried over anhydrous magnesium sulfate
  9. customAfter removing magnesium sulfate
  10. filtrationby filtration
  11. concentrationconcentrating under reduced pressure
  12. washthe resulting crystal was washed with hexane
  13. customdried

Sources & evidence

ORD record
ord-329a00e6aa044be599a6bb7faa9f23f7
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

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