HCID 10017173, Verbindung → HCID 10315149, Verbindung

HRID 1756680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1756680
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][CH2:12][C:13](=[O:21])[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:6][CH2:5]1)(=O)[CH3:2]>Cl>[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][CH2:12][C:13](=[O:21])[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:6][CH2:5]1)[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

3

Edukt 1

HCID 10017173HCID 10017173, Verbindung

Produkt 1

HCID 10315149HCID 10315149, VerbindungAusbeute 161,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

A solution of 1-acetyl-4-[3-(4-fluorobenzoyl)propyl]piperidine (1.7 g) in concentrated hydrochloric acid (15 ml) was refluxed for 16 hours and the hydrochloric acid was then distilled off under reduced pressure. The residue was dissolved in water and the solution was made weakly basic (pH ca.8) with 5% aqueous sodium hydroxide solution and extracted with dichloromethane. The extract was washed with water and dried over anhydrous sodium sulfate and the solvent was distilled off to recover 1.3 g of residue. To a solution of this residue (1.3 g) in ethanol (10 ml) was added 0.94 g of potassium carbonate and 0.9 g of benzyl bromide was added dropwise with ice-cooling. The mixture was stirred at room temperature for 2 hours and then filtered and the filtrate was concentrated under reduced pressure. The residue was diluted with water and extracted with dichloromethane and the extract was washed with water and dried over anhydrous sodium sulfate. Finally the solvent was distilled off to give 1.6 g of 1-benzyl-4-[3-(4-fluorobenzoyl)propyl]piperidine melting at 53°-55° C.

Aufarbeitung

  1. distillationthe hydrochloric acid was then distilled off under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with dichloromethane
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customto recover 1.3 g of residue
  8. additionTo a solution of this residue (1.3 g) in ethanol (10 ml) was added 0.94 g of potassium carbonate and 0.9 g of benzyl bromide
  9. additionwas added dropwise with ice-
  10. temperaturecooling
  11. filtrationfiltered
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. additionThe residue was diluted with water
  14. extractionextracted with dichloromethane
  15. washthe extract was washed with water
  16. dry with materialdried over anhydrous sodium sulfate
  17. distillationFinally the solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-455b68f2bc5840959beb8c2733e74d8d
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05441967

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