Hydrochloric Acid → HCID 21952767, compound

HRID 1677033Notes

Reaction equation

HRID 1677033 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.Cl.[F:9][C:10]([F:20])([F:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17]N.B(F)(F)F.CCOCC>C(O)(=O)C>[F:9][C:10]([F:19])([F:20])[C:11]1[C:12]2[NH:17][C:4]3[CH2:3][CH2:2][NH:1][CH2:6][C:5]=3[C:13]=2[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8000Boron trifluoride etherateHCID 337214-PiperidoneHCID 5208002-(Trifluoromethyl)phenylhydrazine

Product 1

HCID 21952767HCID 21952767, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To 4-piperidone.HCl (1.36 g, 10.0 mmol) and 2-trifluoromethylphenylhydrazine.HCl (2.13 g, 10.0 mmol) in acetic acid (50 mL) was added the 1.0 M borontrifluoride etherate (2.46 mL, 20.0 mmol) and the reaction stirred at 90° C. for 8 hours and then allowed to cool. The mixture was concentrated in vacuo and ethanol (ca 20 mL) added and then cooled to 0° C., the solid was filtered off and the mother liquor was concentrated in vacuo and water (adjusted to pH 14 with 2M NaOH) added to the residue. The solid was filtered off and washed with water and dried under high vacuum.

Workup

  1. temperatureto cool
  2. concentrationThe mixture was concentrated in vacuo and ethanol (ca 20 mL)
  3. additionadded
  4. temperaturecooled to 0° C.
  5. filtrationthe solid was filtered off
  6. concentrationthe mother liquor was concentrated in vacuo and water (adjusted to pH 14 with 2M NaOH)
  7. additionadded to the residue
  8. filtrationThe solid was filtered off
  9. washwashed with water
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-d32a0afef3ed4c07b99964425c4cb01b
Source dataset
uspto-grants-2011_08
Patent number
US08008279B2

Reaction notes

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