Sulfamic Acid → 2-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acid

HRID 2096264Notes

Reaction equation

HRID 2096264 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]=[CH:16][C:15]=2[CH:20]=[O:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)([OH:24])N.[O-]Cl=O.[Na+]>O1CCOCC1.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([OH:24])=[O:21])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 64909901-Boc-4-(2-formylphenyl)piperazineHCID 23668197Sodium Chlorite

Product 1

HCID 27567762-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acidYield 94.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
4 °C

Procedure

4-(2-Formyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.50 g, 1.72 mmol) is dissolved in 80 mL of dioxane and 20 mL of H2O. The mixture is cooled to 4° C. and then sulfamic acid (1.36 g, 14.00 mmol) is added in one portion. The mixture is stirred for an additional 30 min and then 3 mL of a solution of NaClO2 (0.343 g, 3.80 mmol) is added in a drop-wise portion. The reaction is quenched by the addition of 50 mL of H2O and 50 mL of brine. The resulting mixture is extracted with 3×100 mL of CH2Cl2. The combined organic phase is washed with 2×50 mL of brine, dried with MgSO4, filtered and concentrated to give 500 mg of 4-(2-carboxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe reaction is quenched by the addition of 50 mL of H2O and 50 mL of brine
  2. extractionThe resulting mixture is extracted with 3×100 mL of CH2Cl2
  3. washThe combined organic phase is washed with 2×50 mL of brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dbb948dc2e5f4add806b4e1fe67cff83
Source dataset
uspto-grants-2013_05
Patent number
US08450317B2

Reaction notes

Loading…