1-Boc-4-(3-(ethoxycarbonyl)phenyl)piperazine → 3-(4-(Tert-butoxycarbonyl)piperazin-1-yl)benzoic acid

HRID 2047367Notes

Reaction equation

HRID 2047367 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([O:22]CC)=[O:21])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[OH-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([OH:22])=[O:21])[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 162179411-Boc-4-(3-(ethoxycarbonyl)phenyl)piperazine

Product 1

HCID 448287263-(4-(Tert-butoxycarbonyl)piperazin-1-yl)benzoic acidYield 85.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-(3-ethoxycarbonyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (5.00 g, 14.95 mmol) in EtOH (50 mL) and NaOH 10% (20 mL) was refluxed for 3 h, then the reaction mixture was cooled to room temperature and the organic solvent evaporated under reduced pressure. The resulting solution was neutralized by the dropwise addition of 1N HCl and the aqueous solution was extracted with EtOAc (3×50 mL) The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to obtain 3.90 g of the title compound (85%) without further purification.

Workup

  1. customthe organic solvent evaporated under reduced pressure
  2. additionThe resulting solution was neutralized by the dropwise addition of 1N HCl
  3. extractionthe aqueous solution was extracted with EtOAc (3×50 mL) The combined organic layers
  4. dry with materialwere dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-93898ce3a10a4e90865a4477ab808f3b
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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