Ethanol → (1-Benzyl-4-phenylpiperidine-4-carbonyl)-oxidoazanium

HRID 265981

Reaktionsgleichung

Reaktionsgleichung von HRID 265981
[C:1]1([C:7]2([C:20]#[N:21])[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:22].[Na+].C([OH:26])C>>[C:1]1([C:7]2([C:20]([NH2:21]=[O:26])=[O:22])[CH2:8][CH2:9][N:10]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 1914081-Benzyl-4-cyano-4-phenylpiperidine

Produkt 1

HCID 88146759(1-Benzyl-4-phenylpiperidine-4-carbonyl)-oxidoazanium

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

4-Phenyl-4-cyano-1-benzyl-piperidine (535 g, 1940 mmol) was combined with aqueous sodium hydroxide (85 mL, 50% by weight) and ethanol (5 L) and the mixture was heated to 50° C. The heating was removed, and a solution of hydrogen peroxide (856 mL, 30% by weight in water) 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 20 hours. The reaction mixture was diluted with water (3 L) and the ethanol was removed in vacuo at 35° C. Cooling the reaction mixture to ambient temperature gave a solid which was collected by filtration, rinsed with water, and air dried to give 4-phenyl-1-benzyl-piperidine-4-carboxylic acid amide N-oxide.

Aufarbeitung

  1. customThe heating was removed
  2. additiona solution of hydrogen peroxide (856 mL, 30% by weight in water) was added at such a rate that the temperature of the reaction mixture
  3. customdoes not rise above 50° C
  4. additionThe reaction mixture was diluted with water (3 L)
  5. customthe ethanol was removed in vacuo at 35° C
  6. temperatureCooling the reaction mixture to ambient temperature
  7. customgave a solid which
  8. filtrationwas collected by filtration
  9. washrinsed with water, and air
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d70f0213737245e8a75f00f604b80509
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648366

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