Benzofuran → 4-(2-Benzofuranyl)-1,3-dimethyl-4-piperidinol

HRID 745821

Reaktionsgleichung

Reaktionsgleichung von HRID 745821
C([Li])CCC.[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[CH:7]1.[CH3:15][N:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH:18]([CH3:23])[CH2:17]1>CCCCCC.C(OCC)C>[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[C:7]1[C:19]1([OH:22])[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH:18]1[CH3:23]

Komponenten

6

Edukt 3

HCID 9223BenzofuranHCID 1073111,3-Dimethyl-4-piperidoneHCID 178418339Butyllithium

Produkt 1

HCID 233122544-(2-Benzofuranyl)-1,3-dimethyl-4-piperidinol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

50 ml of a bimolar solution of n-butyl lithium in hexane is added dropwise within 30 minutes, at a reaction temperature of -5°, to a solution of 11.8 g of benzofuran in 100 ml of diethyl ether. The solution is then stirred for a further hour at 0°. There is thereupon made within 15 minutes a dropwise addition of a solution of 1,3-dimethyl-4-piperidone in 50 ml of abs. diethyl ether. The reaction temperature is maintained at 0° by external cooling. The reaction solution is subsequently stirred for a further 15 hours at room temperature. It is then poured, with stirring, onto 200 g of ice, and the aqueous phase extracted three times with 500 ml of ethyl acetate each time. The combined organic extracts are dried over sodium sulphate, filtered, and concentrated by evaporation. The residue is dissolved in 500 ml of 2N hydrochloric acid and the acid solution washed with ether. The aqueous solution is thereupon adjusted by addition of 10% sodium hydroxide solution to pH 12, and extracted with 1 liter of chloroform. The chloroform solution is dried with sodium sulphate, filtered off under suction, and concentrated by evaporation to obtain 4-(2-benzofuranyl)-1,3-dimethyl-4-piperidinol, which melts at 128°-130° after recrystallisation from hexane.

Aufarbeitung

  1. temperatureThe reaction temperature is maintained at 0° by external cooling
  2. stirringThe reaction solution is subsequently stirred for a further 15 hours at room temperature
  3. additionIt is then poured
  4. extractionthe aqueous phase extracted three times with 500 ml of ethyl acetate each time
  5. dry with materialThe combined organic extracts are dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. dissolutionThe residue is dissolved in 500 ml of 2N hydrochloric acid
  9. washthe acid solution washed with ether
  10. additionThe aqueous solution is thereupon adjusted by addition of 10% sodium hydroxide solution to pH 12
  11. extractionextracted with 1 liter of chloroform
  12. dry with materialThe chloroform solution is dried with sodium sulphate
  13. filtrationfiltered off under suction
  14. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-f4340b574c3b4dc59c569759814f5989
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04600719

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