Acetone → 4-Methylamino-4-phenylcyclohexanone hydrochloride

HRID 462299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 462299
[CH3:1][NH:2][C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[ClH:16].CC(C)=O.C(=O)(O)[O-].[Na+]>C(OCC)C.C(Cl)Cl>[ClH:16].[CH3:1][NH:2][C:3]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 133452704-Methylamino-4-phenylcyclohexanone

Produkt 1

HCID 204533474-Methylamino-4-phenylcyclohexanone hydrochlorideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel3×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A reaction mixture consisting of 1.0 gm. (0.0035 mole) of 4-methylamino-4-phenylcyclohexanone, ethylene ketal, hydrochloride (prepared in Example 17, Part G, above) 2.0 ml. of 2.5 N hydrochloric acid, and 20 ml. acetone is stirred continuously for 18 hours, at 25° C. The reaction mixture is then made basic by adding solid sodium bicarbonate, and most of the solvent is removed by evaporation under reduced pressure. The concentrated material thus obtained is ectracted four times with 20 ml. portions of methylene chloride. The extracts are combined and the methylene chloride is removed by evaporation under reduced pressure. A gummy residue is obtained that is dissolved in diethyl ether. The ether solution is treated with hydrogen chloride in ether. A precipitate forms which is collected on a filter and recrystallized from a mixture of methylene chloride and ethyl acetate. There is thus obtained 0.53 gm. (74% yield) of 4-methylamino-4-phenylcyclohexanone hydrochloride having a melting range from 218° to 220° C.

Aufarbeitung

  1. custommost of the solvent is removed by evaporation under reduced pressure
  2. customThe concentrated material thus obtained
  3. customthe methylene chloride is removed by evaporation under reduced pressure
  4. customA gummy residue is obtained
  5. customA precipitate forms which is collected on
  6. filtrationa filter
  7. customrecrystallized from a mixture of methylene chloride and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f7dbebc6a0f247e5a9ba025260127473
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04065573

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