Hydrogen Peroxide → (1s,2s,5e)-5-Benzylidene-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexanecarboxylic acid

HRID 61490

Reaction equation

HRID 61490 reaction equation
[CH:1](=[C:8]1/[CH2:9][CH2:10][C@H:11]([C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:22][CH2:21]2)=[O:19])[C@@H:12]([C:14]([O:16]C)=[O:15])[CH2:13]/1)/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[OH-].[Li+].O.OO>>[CH:1](=[C:8]1/[CH2:9][CH2:10][C@H:11]([C:18]([N:20]2[CH2:21][CH2:22][N:23]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:24][CH2:25]2)=[O:19])[C@@H:12]([C:14]([OH:16])=[O:15])[CH2:13]/1)/[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 784Hydrogen PeroxideHCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67304520Methyl (1s,2s,5e)-5-benzylidene-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexanecarboxylate

Product 1

HCID 67304377(1s,2s,5e)-5-Benzylidene-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexanecarboxylic acid

Procedure

To a stirred solution of methyl(1S,2S,5E)-5-benzylidene-2-[(4-phenylpiperazin-1-yl)carbonyl]cyclohexanecarboxylate (116 mg, 0.000277 mol) in tetrahydrofuran (6.0 mL, 0.074 mol) at rt was added a solution of lithium hydroxide (102 mg, 0.00416 mol) in water (2.0 mL, 0.11 mol). The resulting cloudy solution was stirred at rt for 17 h. LCMS showed that there was only 40% conversion. The reaction mixture was cooled to 0° C., hydrogen peroxide (0.113 mL, 0.00111 mol) was then added. The reaction mixture was stirred at 0° C. for 2 h. LCMS showed that there was little change. The reaction mixture was then stirred at rt over the weekend. LCMS showed the reaction was done. The reaction was quenched with 10% Na2S2O3 (10 mL), acidified with 1 N HCl (5 mL) to pH=4, extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give the desired product as a colorless solid. (112 mg, 100% in yield). MS (ESI): (M+H)+=405.1.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringThe reaction mixture was stirred at 0° C. for 2 h
  3. stirringThe reaction mixture was then stirred at rt over the weekend
  4. customThe reaction was quenched with 10% Na2S2O3 (10 mL)
  5. extractionextracted with EtOAc (2×)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-42820b3cf2fe4250bd11b205ddeb08d5
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Linked notes

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