Hydrochloric Acid → 4-Phenyl-4-piperidinocyclohexanone

HRID 1462516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1462516
Cl.C1[O:18][C:5]2([CH2:10][CH2:9][C:8]([NH2:17])([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)OC1.I[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]I.C(=O)([O-])[O-].[K+].[K+].Cl>C(OCC)C.O.C(O)C>[C:11]1([C:8]2([N:17]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:7][CH2:6][C:5](=[O:18])[CH2:10][CH2:9]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric Acid2×HCID 11430Potassium CarbonateHCID 123541,5-DiiodopentaneHCID 85930704HCID 85930704, Verbindung

Produkt 1

HCID 133067564-Phenyl-4-piperidinocyclohexanoneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel4×

Versuchsvorschrift

A reaction mixture consisting of the free base from 2.88 gm. (0.011 mole) of 4-amino-4-phenylcyclohexanone ethylene ketal hydrochloride (prepared in Example 32, above), 3.47 gm. 1,5-diiodopentane 2.95 gm. potassium carbonate and 25 ml. ethanol is heated at the reflux temperature, with stirring, for eighteen (18) hours. After cooling and removing most of the liquid and voltiles by evaporation under reduced pressure, the residue thus obtained is dispersed in a mixture of 100 ml. of diethyl ether and 10 ml. of water. The ether layer is allowed to separate and is recovered. It is washed with water and with brine, before removing the ether by evaporation under reduced pressure. The residue thus obtained is dissolved in diethyl ether and an amount of 3 N hydrogen chloride in diethyl ether is added so as to form the hydrochloride acid addition salt which precipitates. The salt is collected on a filter and then recrystallized from a mixture of methylene chloride and ethyl acetate. There is thus obtained 2.26 gm. (61% yield) of 4-phenyl-4-(1-piperidinyl)cyclohexanone, ethylene ketal hydrochloride having a melting range from 228° to 231° C. An analytical sample has a melting point at 234° to 235.5° C.

Aufarbeitung

  1. temperatureAfter cooling
  2. customremoving most of the liquid and voltiles by evaporation under reduced pressure
  3. customthe residue thus obtained
  4. additionis dispersed in a mixture of 100 ml
  5. customto separate
  6. customis recovered
  7. washIt is washed with water and with brine
  8. custombefore removing the ether
  9. customby evaporation under reduced pressure
  10. customThe residue thus obtained
  11. customto form
  12. customprecipitates
  13. customThe salt is collected on
  14. filtrationa filter
  15. customrecrystallized from a mixture of methylene chloride and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-dc4daf26cb6649e1993d1511cf85a363
Quelldatensatz
uspto-grants-1984_07
Patentnummer
US04460604

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