Sodium Hydroxide → {4-[2-(3,5-Dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzoic acid

HRID 2096262

Reaktionsgleichung

Reaktionsgleichung von HRID 2096262
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:25])[CH2:17][N:18]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[N:19]2)[CH2:12][CH2:11]1.[OH-].[Na+]>C1COCC1.CO>[CH3:24][C:20]1[CH:21]=[C:22]([CH3:23])[N:18]([CH2:17][C:16]([N:13]2[CH2:14][CH2:15][N:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:26])=[O:2])[CH2:11][CH2:12]2)=[O:25])[N:19]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 665997292-{4-[2-(3,5-Dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzoic acid methyl ester

Produkt 1

HCID 57516317{4-[2-(3,5-Dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzoic acidAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

2-{4-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzoic acid methyl ester (0.848 g, 2.38 mmol) is dissolved in 10 mL of 1:1 THF/MeOH. 2 mL of 15% aq NaOH is added and the mixture is stirred overnight. The mixture is concentrated to dryness and suspended in 50 mL of H2O. The pH of the solution is adjusted to 4 by careful addition of conc. HCl. The aqueous phase is extracted with 3×100 mL of CH2Cl2. The organic phase is dried with MgSO4, filtered and concentrated to give 0.730 g of {4-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzoic acid in 90% yield.

Aufarbeitung

  1. concentrationThe mixture is concentrated to dryness
  2. additionThe pH of the solution is adjusted to 4 by careful addition of conc. HCl
  3. extractionThe aqueous phase is extracted with 3×100 mL of CH2Cl2
  4. dry with materialThe organic phase is dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-18c3207e43794d17933259829d69c8a5
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450317B2

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