1-Benzyl-4-piperidone → HCID 5297706, compound

HRID 2303979Notes

Reaction equation

HRID 2303979 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:10]([N:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C>C(OCC)(=O)C>[NH2:5][C:4]1[C:19]2[CH2:18][N:17]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:22][CH2:21][C:20]=2[N:1]=[C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=12

Participants

5

Reactant 3

HCID 192201-Benzyl-4-piperidoneHCID 65367Trimethylsilyl triflateHCID 729132-Aminobenzonitrile

Product 1

HCID 5297706HCID 5297706, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

11.55 g (97.80 mmol) of 2-aminobenzonitrile and 24.07 g (127.14 mmol) of N-benzylpiperidine-4-one were dissolved in 200 ml of ethyl acetate, to which 50.00 g (225.00 mmol) of trimethylsilyltrifluoromethane sulfonate was added dropwise at room temperature. After the end of the dropwise addition, the mixture was refluxed under heating for 6 hours. After air cooling, the produced crystals were filtered out and washed with 320 ml of ethyl acetate. The obtained crystals were dried, added to a mixed solution of 400 ml of water and 200 ml of ethanol and dissolved by heating. After air cooling, 250 ml of a 1N sodium hydroxide solution was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution and dried over anhydrous sodium sulfate, and then the drying agent was filtered out. The filtrate was concentrated under reduced pressure and the residue was suspended in a mixed solution of 200 ml of ethyl acetate and 200 ml of hexane. The produced crystals were filtered out and further washed with the above mixed solution to obtain the title compound (27.39 g, 95% yield).

Workup

  1. additionwas added dropwise at room temperature
  2. additionAfter the end of the dropwise addition
  3. temperaturethe mixture was refluxed
  4. temperatureunder heating for 6 hours
  5. temperatureAfter air cooling
  6. filtrationthe produced crystals were filtered out
  7. washwashed with 320 ml of ethyl acetate
  8. customThe obtained crystals were dried
  9. additionadded to a mixed solution of 400 ml of water and 200 ml of ethanol
  10. dissolutiondissolved
  11. temperatureby heating
  12. temperatureAfter air cooling
  13. addition250 ml of a 1N sodium hydroxide solution was added
  14. extractionthe mixture was extracted with ethyl acetate
  15. washThe organic layer was washed with a saturated saline solution
  16. dry with materialdried over anhydrous sodium sulfate
  17. filtrationthe drying agent was filtered out
  18. concentrationThe filtrate was concentrated under reduced pressure
  19. filtrationThe produced crystals were filtered out
  20. washfurther washed with the above mixed solution

Sources & evidence

ORD record
ord-0b40e2cade5f4c43b49adaec71ad1857
Source dataset
uspto-grants-2002_08
Patent number
US06433174B1

Reaction notes

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