Diethyl Ether → 4-(3-Trifluoromethylbenzoyl)piperidine

HRID 2420494

Reaktionsgleichung

Reaktionsgleichung von HRID 2420494
Br[C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][CH:7]=1.[Mg].C([N:16]1[CH2:21][CH2:20][CH:19]([C:22]#N)[CH2:18][CH2:17]1)(=O)C.[Cl-].[NH4+].CC[O:28]CC>O1CCCC1>[F:9][C:8]([F:11])([F:10])[C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:22]([CH:19]1[CH2:18][CH2:17][NH:16][CH2:21][CH2:20]1)=[O:28]

Komponenten

7

Edukt 5

HCID 3283Diethyl Ether2×HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 25517Ammonium ChlorideHCID 27562861-Acetylpiperidine-4-carbonitrileHCID 5462224Magnesium

Produkt 1

HCID 50864474-(3-Trifluoromethylbenzoyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(3-trifluoromethylbenzoyl)piperidine is prepared in the following manner: A solution of 102.5 g of 3-bromobenzotrifluoride in 25 ml of ether is added dropwise to a stirring mixture of 11.5 g of magnesium turnings in 300 ml of anhydrous ether to maintain a moderate reflux. After total addition the resulting dark mixture is stirred for 1 hour at ambient temperature. A solution of 60.0 g of 1-acetyl-4-cyanopiperidine in 100 ml of tetrahydrofuran is slowly added to this mixture and the mixture is stirred for 16 hours. An excess of an aqueous solution of ammonium chloride is added and the mixture is heated on a steam bath for 3 hours. The mixture is allowed to cool, extracted with benzene and the combined extracts are dried. The solvent is removed and the residue is dissolved in ethanol and basified with sodium hydroxide. The alkaline solution is refluxed for 3 hours, cooled and extracted with benzene. The combined benzene extracts are dried and the benzene is removed, leaving the oil, 4(3 -trifluoromethylbenzoyl)piperidine, which is converted to the hydrochloride, mp. 196°-198° C.

Aufarbeitung

  1. custom4-(3-trifluoromethylbenzoyl)piperidine is prepared in the following manner
  2. temperatureto maintain a moderate reflux
  3. additionAfter total addition the resulting dark mixture
  4. stirringthe mixture is stirred for 16 hours
  5. temperaturethe mixture is heated on a steam bath for 3 hours
  6. temperatureto cool
  7. extractionextracted with benzene
  8. customthe combined extracts are dried
  9. customThe solvent is removed
  10. dissolutionthe residue is dissolved in ethanol and basified with sodium hydroxide
  11. temperatureThe alkaline solution is refluxed for 3 hours
  12. temperaturecooled
  13. extractionextracted with benzene
  14. dry with materialThe combined benzene extracts are dried
  15. customthe benzene is removed

Quellen und Nachweise

ORD-Eintrag
ord-5596da805c504eb5a4747c0791f318f7
Quelldatensatz
uspto-grants-1978_08
Patentnummer
US04110459

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