Hydrochloric Acid → 1-Benzoylpiperidine-4-carboxylic acid

HRID 278247

Reaktionsgleichung

Reaktionsgleichung von HRID 278247
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1.[OH-].[Na+].[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>O>[C:12]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 37734-Piperidinecarboxylic acidHCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide

Produkt 1

HCID 789351-Benzoylpiperidine-4-carboxylic acidAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 10 g of isonipecotic acid in 100 mL of water was added 31 mL of 5 N NaOH at 0° C. The reaction was warmed to room temperature and stirred for 0.5 h. The reaction was again cooled to 0° C. and 11.97 g of benzoyl chloride was added. The reaction was then warmed to room temperature and stirred for 1.5 h. Concentrated HCl was then added until a precipitate formed. The mixture was extracted with 3×150 mL of ethyl acetate and the combined organic layers were dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was dissolved in methylene chloride. Ether was then slowly added to precipitate the product which was filtered to give 8 g of the title compound.

Aufarbeitung

  1. temperatureThe reaction was again cooled to 0° C.
  2. temperatureThe reaction was then warmed to room temperature
  3. stirringstirred for 1.5 h
  4. customformed
  5. extractionThe mixture was extracted with 3×150 mL of ethyl acetate
  6. dry with materialthe combined organic layers were dried over magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. dissolutionthe residue was dissolved in methylene chloride
  9. additionEther was then slowly added
  10. customto precipitate the product which
  11. filtrationwas filtered

Quellen und Nachweise

ORD-Eintrag
ord-fbe54d05da7f4ef39586a033f1f63d51
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358979B1

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