Hydrochloric Acid → {4-[3-(3,4,5-Trimethoxy-phenyl)-propionyl]piperazin-1-yl}-acetic acid

HRID 1944260

Reaktionsgleichung

Reaktionsgleichung von HRID 1944260
C([O:3][C:4](=[O:28])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:27])[CH2:13][CH2:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH2:8][CH2:7]1)C.[OH-].[Na+].Cl>CO.CCOC(C)=O>[CH3:26][O:25][C:17]1[CH:16]=[C:15]([CH2:14][CH2:13][C:12]([N:9]2[CH2:8][CH2:7][N:6]([CH2:5][C:4]([OH:28])=[O:3])[CH2:11][CH2:10]2)=[O:27])[CH:20]=[C:19]([O:21][CH3:22])[C:18]=1[O:23][CH3:24]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59785706{4-[3-(3,4,5-Trimethoxy-phenyl)-propionyl]-piperazin-1-yl}-acetic acid ethyl ester

Produkt 1

HCID 59785715{4-[3-(3,4,5-Trimethoxy-phenyl)-propionyl]piperazin-1-yl}-acetic acidAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dissolve {4-[3-(3,4,5-Trimethoxy-phenyl)-propionyl]-piperazin-1-yl}-acetic acid ethyl ester (45) (100 mg, 0.25 mmol) in MeOH (2.0 mL) at rt and add 2M aqu NaOH (260 μL, 0.52 mmol). Stir the reaction mixture for 1 h under reflux. Add dropwise 1M aqu. HCl (550 μL, 0.55 mmol), extract the mixture with EtOAc (3 times) and remove solvent obtain {4-[3-(3,4,5-Trimethoxy-phenyl)-propionyl]-piperazin-1-yl}-acetic acid (46) (88 mg, 95%) as a brown sticky solid. No further purification. 1H NMR (400 MHz, CDCl3/CD3OD 9+1): 2.54 (br.t, 2H); 2.78 (t, 2H, J=7.5 Hz); 2.83-3.10 (br.m, 2H); 3.24 (s, 2H); 3.43-3.62 (br.m, 2H); 3.68 (s, 3H); 3.73 (s, 6H); 3.74-3.85 (br.m, 4H); 6.34 (s, 2H).

Aufarbeitung

  1. temperatureunder reflux
  2. additionAdd dropwise 1M aqu
  3. customremove solvent

Quellen und Nachweise

ORD-Eintrag
ord-c0132e206c55402a9e1d56b1e6ef3d07
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394835B2

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