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

HRID 541213

反応式

HRID 541213 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d78db4fd50eb494ba41e46b80d0ab06d
出典データセット
uspto-grants-2014_10
特許番号
US08871790B2

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