Sodium Hydroxide → 4-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acid

HRID 1776016Notes

Reaction equation

HRID 1776016 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22]CC)=[O:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([OH:22])=[O:21])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11709764tert-Butyl 4-(4-(ethoxycarbonyl)phenyl)piperazine-1-carboxylate

Product 1

HCID 27955084-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acidYield 87.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 4-(4-ethoxycarbonyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (10 g, 29.9 mmol) in ethanol (200 mL was added 1 N sodium hydroxide (100 mL). The reaction mixture was stirred at 70° C. overnight. The solvent was removed under vacuum and the residue washed twice with ethyl acetate, acidified to pH 6 with 5 N HCl, filtered, and concentrated to dryness to provide the title compound (8 g, 87% yield) as a white solid. 1H NMR (d6-DMSO, 400 MHz) δ (ppm) 7.74 (m, 2H), 6.92 (m, 2H), 3.90 (m, 2H), 3.42 (m, 2H), 3.25 (m, 4H), 1.38 (s, 9H).

Workup

  1. customThe solvent was removed under vacuum
  2. washthe residue washed twice with ethyl acetate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ff25cd93e3c24d79a65a5cbabab22646
Source dataset
uspto-grants-2016_02
Patent number
US09260414B2

Reaction notes

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