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

HRID 541340Notes

Reaction equation

[CH2:1]([C:3]1[CH:24]=[C:23]([CH3:25])[C:22]([CH:26]=[O:27])=[CH:21][C:4]=1[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:2].[O-:28][Mn](=O)(=O)=O.[K+]>O1CCCC1.O>[C:17]([C:16]1[CH:19]=[CH:20][C:13]([CH:10]2[CH2:9][CH2:8][N:7]([C:5]([C:4]3[C:3]([CH2:1][CH3:2])=[CH:24][C:23]([CH3:25])=[C:22]([CH:21]=3)[C:26]([OH:28])=[O:27])=[O:6])[CH2:12][CH2:11]2)=[CH:14][CH:15]=1)#[N:18]

Participants

Conditions

Temperature: 60 °C

Procedure

To a round-bottom flask was added a solution of 4-(1-(2-ethyl-5-formyl-4-methylbenzoyl)piperidin-4-yl)benzonitrile (compound 211.5, 720 mg, 2.00 mmol, 1.00 equiv) in tetrahydrofuran (20 mL). A solution of KMnO4 (640 mg, 4.05 mmol, 2.00 equiv) in water (20 mL) was added dropwise. The resulting solution was stirred for 15 h at 60° C. then cooled to rt with a water bath. The solids were removed with filtration. The filtrate was extracted with 3×30 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. This resulted in 600 mg (80%) of 5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-4-ethyl-2-methylbenzoic acid as a light yellow solid.

Workup

temperaturethen cooled to rt with a water bath
customThe solids were removed with filtration
extractionThe filtrate was extracted with 3×30 mL of ethyl acetate
dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThis resulted in 600 mg (80%) of 5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-4-ethyl-2-methylbenzoic acid as a light yellow solid

Sources & evidence

ORD record: ord-673184df687d4b41b37eeb3826a08613
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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