Hydrochloric Acid → Piperazine, 1-(3,4-dihydroxybenzoyl)-4-methyl-

HRID 1734266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1734266
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:23])[C:9]2[CH:14]=[CH:13][C:12]([O:15]C(=O)C)=[C:11]([O:19]C(=O)C)[CH:10]=2)[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:23])[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([OH:19])[CH:10]=2)[CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 150773061-Methyl-4-(3,4-diacetoxybenzoyl)piperazine

Produkt 1

HCID 3062451Piperazine, 1-(3,4-dihydroxybenzoyl)-4-methyl-Ausbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of 1-methyl-4-(3,4-diacetoxybenzoyl)piperazine (295 mg) in methanol (3 ml) was added a saturated potassium carbonate solution in methanol (6 ml) and the mixture was stirred at room temperature for 30 minutes. The mixture was poured into ice water and adjusted to pH 9 with 1N hydrochloric acid. The mixture was extracted several times with a mixture of chloroform and methanol (20:1 V/V) and the organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized by addition of ethyl acetate to give 1-methyl-4-(3,4-dihydroxybenzoyl)piperazine (71 mg) as white crystal.

Aufarbeitung

  1. extractionThe mixture was extracted several times
  2. additionwith a mixture of chloroform and methanol (20:1 V/V)
  3. washthe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized by addition of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-91322c5ef7ca450f8623e54b39d6d5f7
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05532354

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