Piperonylamine → HCID 380002, compound

HRID 864484Notes

Reaction equation

HRID 864484 reaction equation
O.Cl.[NH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.Cl.[F:11][C:12]1[CH:13]=[C:14]([NH:18]N)[CH:15]=[CH:16][CH:17]=1>C(O)C>[F:11][C:12]1[CH:17]=[CH:16][C:15]2[C:7]3[CH2:8][NH:3][CH2:4][CH2:5][C:6]=3[NH:18][C:14]=2[CH:13]=1

Participants

4

Reactant 2

HCID 2723901PiperonylamineHCID 27239143-Fluorophenylhydrazine hydrochloride

Product 1

HCID 380002HCID 380002, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Piperidone hydrochloride monohydrate (4.55 g) and 3-fluorophenylhydrazine hydrochloride (4.85 g) were added to ethanol (80 ml) and the mixture was heated under reflux for one hour. Hydrogen chloride gas was bubbled into the mixture and refluxing was recommenced for another 1.5 hours. The solution was cooled to 0° C., the hydrochloride was filtered off, washed with ethanol, dissolved in boiling water, decolourised with activated charcoal and filtered. 2M Sodium hydroxide solution was added to the warm solution until it was neutral when tested with pH paper. The pale cream solid was filtered off, washed with water and dried. Recrystallisation from acetonitrile gave a white solid which was a mixture of 7-fluoro and 9-fluoro-isomers in a ratio of 86:14 respectively (HPLC).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one hour
  3. customHydrogen chloride gas was bubbled into the mixture
  4. temperaturerefluxing
  5. filtrationthe hydrochloride was filtered off
  6. washwashed with ethanol
  7. dissolutiondissolved
  8. filtrationfiltered
  9. addition2M Sodium hydroxide solution was added to the warm solution until it
  10. filtrationThe pale cream solid was filtered off
  11. washwashed with water
  12. customdried
  13. customRecrystallisation from acetonitrile
  14. customgave a white solid which
  15. additiona mixture of 7-fluoro and 9-fluoro-isomers in a ratio of 86:14 respectively (HPLC)

Sources & evidence

ORD record
ord-58df874c4bff4fd2a6e4f8333825432c
Source dataset
uspto-grants-1996_10
Patent number
US05563147

Reaction notes

Loading…