Potassium Permanganate → 5-(4-(4-Cyanophenyl)piperidine-1-carbonyl)-2-methylbenzoic acid

HRID 541213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541213
[CH:1]([C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])=[O:2].[O-:26][Mn](=O)(=O)=O.[K+]>C1COCC1.O>[C:18]([C:17]1[CH:16]=[CH:15][C:14]([CH:11]2[CH2:12][CH2:13][N:8]([C:6]([C:5]3[CH:22]=[CH:23][C:24]([CH3:25])=[C:3]([CH:4]=3)[C:1]([OH:26])=[O:2])=[O:7])[CH2:9][CH2:10]2)=[CH:21][CH:20]=1)#[N:19]

Komponenten

5

Edukt 2

HCID 516875Potassium PermanganateHCID 866725244-(1-(3-Formyl-4-methylbenzoyl)piperidin-4-yl)benzonitrile2×

Produkt 1

HCID 682883815-(4-(4-Cyanophenyl)piperidine-1-carbonyl)-2-methylbenzoic acidAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred mixture of 4-(1-(3-formyl-4-methylbenzoyl)piperidin-4-yl)benzonitrile (compound 39.2, 600 mg, 1.81 mmol, 1.00 equiv) in THF (5 mL) was added dropwise a solution of KMnO4 (1 g) in water (10 mL). The resulting mixture was stirred overnight at 60° C. in an oil bath. After cooling to ambient temperature, the solids were removed by filtration and the pH of the filtrate was adjusted to ≧10 with sodium hydroxide (aqueous, 1 M). The resulting mixture was washed with 20 mL of ethyl acetate. Aqueous 1 M HCl was then employed to adjust the pH of the aqueous layer to ˜4. The resulting aqueous phase was extracted with 2×100 mL of ethyl acetate and the combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 500 mg (80%) of the title compound as light yellow oil.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. customthe solids were removed by filtration
  3. washThe resulting mixture was washed with 20 mL of ethyl acetate
  4. extractionThe resulting aqueous phase was extracted with 2×100 mL of ethyl acetate
  5. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d78db4fd50eb494ba41e46b80d0ab06d
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871790B2

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