Hydrochloric Acid → 3-Ethyl-4-(1-piperidinyl)benzoic acid

HRID 2189740Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2189740
[CH2:1]([C:3]1[CH:4]=C([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)C#N)[CH3:2].[OH-:17].[K+].Cl.[CH2:20]([OH:22])[CH3:21]>O>[CH2:1]([C:3]1[CH:4]=[C:21]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:20]([OH:17])=[O:22])[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium Hydroxide2×HCID 593167193-Ethyl-4-(1-piperidinyl)benzonitrile

Produkt 1

HCID 593167883-Ethyl-4-(1-piperidinyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

3-Ethyl-4-(1-piperidinyl)benzonitrile (D8) (817 mg, 3.82 mmol) and potassium hydroxide (2.14 g, 38.2 mmol) in ethanol (35 mL) and water (8 mL) were heated to 90° C. (block temperature) for 9 h. Further potassium hydroxide (2.14 g, 38.2 mmol) and water (8 mL) were added and the reaction heated for a further 18 h. The reaction was allowed to cool and was neutralised with aqueous HCl. A white solid was separated by filtration and an attempt was made to purify the filtrate by SCX cartridge, but this failed. Both the solid and product of SCX were combined, methanol added and then the mixture acidified with acetic acid. The mixture was filtered to obtain the filtrate, which was then trapped on SCX cartridge, washed with methanol and eluted with 2M ammonia in methanol. On test scale this gave the title compound as a white solid (96 mg, 0.41 mmol) and on the remaining material gave a colourless oil (563 mg, 2.41 mmol). MS (ES): C14H19NO2 requires 233; found 234 (MH+).

Aufarbeitung

  1. temperaturethe reaction heated for a further 18 h
  2. temperatureto cool
  3. customA white solid was separated by filtration
  4. customto purify the filtrate by SCX cartridge
  5. additionmethanol added
  6. filtrationThe mixture was filtered
  7. customto obtain the filtrate, which
  8. washwashed with methanol
  9. washeluted with 2M ammonia in methanol

Quellen und Nachweise

ORD-Eintrag
ord-6aad4414bb974d14b72e67d44b8c9bd1
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324254B2

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