Ethanol → [1-Benzyl-4-(4-fluorophenyl)piperidine-4-carbonyl]-oxidoazanium

HRID 1683121Notes

Reaction equation

HRID 1683121 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)([C:15]#[N:16])[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-:24].[Na+].C(O)C.[OH:29]O>O>[CH2:2]([N:9]1[CH2:10][CH2:11][C:12]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)([C:15]([NH2:16]=[O:29])=[O:24])[CH2:13][CH2:14]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 67560689HCID 67560689, compound

Product 1

HCID 88283475[1-Benzyl-4-(4-fluorophenyl)piperidine-4-carbonyl]-oxidoazanium

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1-Benzyl-4-(4-fluoro-phenyl)-4-cyano-piperidine hydrochloride (7.8 g, 26.5 mmol) was combined with aqueous sodium hydroxide (1.2 mL, 50% by weight) and ethanol (130 mL) and the mixture was heated to 50° C. The heating was removed, and a solution of hydrogen peroxide (12.11 mL, 30% by weight in water, 106 mmol) was added at such a rate that the temperature of the reaction mixture does not rise above 50° C. The reaction mixture was then stirred at 50° C. for 4 hours. The reaction mixture was diluted with water (100 mL) and most of the solvent was removed in vacuo before adding water (200 mL) to form a solid which was collected by filtration, rinsed with water, and dried in vacuo to give the title compound.

Workup

  1. customThe heating was removed
  2. customdoes not rise above 50° C
  3. customwas removed in vacuo
  4. additionbefore adding water (200 mL)
  5. customto form a solid which
  6. filtrationwas collected by filtration
  7. washrinsed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-4a5125ad5f404045b57a0b4428eeaafd
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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