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CAS No. : | 444582-90-5 | MDL No. : | MFCD04115068 |
Formula : | C16H22N2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SSBZXKJSOFJQBW-UHFFFAOYSA-N |
M.W : | 306.36 | Pubchem ID : | 2756776 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: With aminosulfonic acid In 1,4-dioxane; water at 4℃; for 0.5 h; Stage #2: With sodium chlorite In 1,4-dioxane; water |
An alternative method for preparing this intermediate is as follows. 4-(2-Formyl- phenyl)-piperazine-l-carboxylic acid tert-buty\\ 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. To this is added sulfamic acid (1.36 g, 14.00 mmol) in one portion. The mixture is stirred for an additional 30 min. To this is added 3 mL of a solution of NaClO2 (0.343 g, 3.80 mmol) in a dropwise manner. The reaction is quenched reaction with addition of 50 mL of H2O and 50 mL of brine. The mixture is extracted with 3x100 mL of CH2Cl2. The organic phase is washed with 2x50 niL of brine, dried (MgSO4), filtered and concentrated to give 500 mg of 4-(2-carboxy-phenyl)-piperazine-l-carboxylic acid tert-butyl ester, 95 percent yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile | Example 1: Synthesis of 2-{4-[2-(3,5-dimethyl-pyrazol-l-yl)-acetyl]-piperazin-l-yl}- N-phenyl-benzamide 2-Piperazin-l-yl-benzoic acid (2.000 g, 9.79 mmol) is suspended in 100 niL Of CH2Cl2. To this is added diisopropylethyl amine (2.22 niL, 12.00 mmol) and BOC anhydride (2.07 g, 9.50 mmol). After 1 hour, an additional 100 mL of anhydrous CH3CN is added and the mixture is stirred overnight. The mixture is diluted with 250 mL of EtOAc, followed by 250 mL of sat. NH4Cl. The organic phase is washed with 2x250 mL of H2O and 1x250 mL of brine. The organic phase is dried with MgSO4, filtered and concentrated to give 2.37 g of 4-(2-carboxy-phenyl)-piperazine-l-carboxylic acid tert- butyl ester, 80 percent yield. |