Potassium Hydroxide → HCID 22181141, compound

HRID 1268203Notes

Reaction equation

HRID 1268203 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[C:24]([O:26]CC)=[O:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[C:24]([OH:26])=[O:25])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22181030HCID 22181030, compound

Product 1

HCID 22181141HCID 22181141, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-ethoxycarbonylnitrobenzene (1.0 g) in ethanol (10 ml) was added aqueous potassium hydroxide solution (0.2 g in 0.5 ml) and the mixture was heated under reflux for 2 hours. After neutralization with 1M hydrochloric acid, the reaction mixture was extracted with ethyl acetate. The extract was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo to give the desired compound (0.9 g, yield 96%) as a yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionAfter neutralization with 1M hydrochloric acid, the reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-037b15e735d74b95b2b501b0d750fa6c
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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