Sodium Carbonate → (+/-)-1-(cis-2-Phenyl-cyclohexyl)-piperidin-4-one

HRID 348538

Reaktionsgleichung

Reaktionsgleichung von HRID 348538
[C:1]1([C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[N:13]2[CH2:22][CH2:21][C:16]3(OCC[O:17]3)[CH2:15][CH2:14]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+]>CO.Cl>[C:1]1([C@H:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]2[N:13]2[CH2:22][CH2:21][C:16](=[O:17])[CH2:15][CH2:14]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 10340Sodium CarbonateHCID 69486512(+/-)-8-(cis 2-Phenyl-cyclohexyl)-1,4-dioxa-8-aza-spiro[4,5]decane

Produkt 1

HCID 69486592(+/-)-1-(cis-2-Phenyl-cyclohexyl)-piperidin-4-oneAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (+/−)-8-(cis 2-phenyl-cyclohexyl)-1,4-dioxa-8-aza-spiro[4,5]decane (44.8 g) in MeOH (100 ml) and 6N HCl (445 ml) was heated to reflux for 16 h. The reaction mixture was then made basic with solid sodium carbonate, extracted with dichloromethane, dried over sodium sulphate, filtered and evaporated. The crude product was purified by flash chromatography over silica gel with n-heptane as eluent. (+/−)-1-(cis-2-phenyl-cyclohexyl)-piperidin-4-one (28.8 g, 75%) was obtained as a sticky yellow oil, MS (ISP): m/e=258.3 (M+H+).

Aufarbeitung

  1. temperatureto reflux for 16 h
  2. extractionextracted with dichloromethane
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography over silica gel with n-heptane as eluent

Quellen und Nachweise

ORD-Eintrag
ord-3c13606a6f0e4b3a8fc649fc7bd67477
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176316B2

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