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

HRID 541213

반응식

HRID 541213 반응식
[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]

참가 물질

5

반응물 2

HCID 516875Potassium PermanganateHCID 866725244-(1-(3-Formyl-4-methylbenzoyl)piperidin-4-yl)benzonitrile2회

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d78db4fd50eb494ba41e46b80d0ab06d
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871790B2

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