Carbon Dioxide → 2-Dibenzofuranyl 2-piperidylmethyl ketone

HRID 1579508

Reaktionsgleichung

Reaktionsgleichung von HRID 1579508
C(=O)([O-])OC.[Mg+2].COC(=O)[O-].[C:12]([C:15]1[CH:27]=[CH:26][C:18]2[O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:17]=2[CH:16]=1)(=[O:14])[CH3:13].[N:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH:33]=1.C(=O)=O.Cl>CO>[NH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH:33]1[CH2:13][C:12]([C:15]1[CH:27]=[CH:26][C:18]2[O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:17]=2[CH:16]=1)=[O:14]

Komponenten

7

Edukt 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 681612,3,4,5-TetrahydropyridineHCID 167017Carbonic acid, monomethyl ester, magnesium salt (2:1)HCID 2930282-Acetyldibenzofuran

Produkt 1

HCID 123005072-Dibenzofuranyl 2-piperidylmethyl ketoneAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Magnesium methyl carbonate (0.6 mole, 2.5 N in dimethylformamide) is heated to 120°C. under an atmosphere of carbon dioxide. The compound 2-acetyldibenzofuran, 31.5 g (0.15 mole) is added and the mixture is stirred at 120°C. for a period of 4 hours under a stream of nitrogen to form the chelate, allowing the methyl alcohol that forms to escape. The mixture is cooled to room temperature under an atmosphere of carbon dioxide and 15.2 g (0.18 mole) of 2,3,4,5-tetrahydropyridine (as α-tripiperidine) is added and the mixture stirred at room temperature for a period of 40 hours in an atmosphere of carbon dioxide. The resulting mixture is poured into 200 ml of concentrated HCl on 600 g of ice. After standing for 48 hours the precipitate which forms is filtered and washed with ethyl ether. The 2-dibenzofuranyl-2-piperidylmethyl ketone so prepared is twice recrystallized from isopropyl alcohol as the hydrochloride salt and is obtained in 32% yield (16.0 g) and has a M.P. of 218-20°C. (dec.)

Aufarbeitung

  1. customto form the chelate
  2. temperatureThe mixture is cooled to room temperature under an atmosphere of carbon dioxide
  3. waitAfter standing for 48 hours
  4. filtrationthe precipitate which forms is filtered
  5. washwashed with ethyl ether
  6. customThe 2-dibenzofuranyl-2-piperidylmethyl ketone so prepared
  7. customis twice recrystallized from isopropyl alcohol as the hydrochloride salt
  8. customis obtained in 32% yield (16.0 g)

Quellen und Nachweise

ORD-Eintrag
ord-01651cfff3bb4c8482ebafc4ee0219f3
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03931155

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