2,3,5-Trifluorobenzaldehyde → 2-(4-Tert-butylpiperazin-1-yl)-3,5-difluorobenzaldehyde

HRID 1695918

Reaktionsgleichung

Reaktionsgleichung von HRID 1695918
[C:1]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].F[C:12]1[C:19]([F:20])=[CH:18][C:17]([F:21])=[CH:16][C:13]=1[CH:14]=[O:15].O.C(OCC)(=O)C>O1CCOCC1>[C:1]([N:5]1[CH2:10][CH2:9][N:8]([C:12]2[C:19]([F:20])=[CH:18][C:17]([F:21])=[CH:16][C:13]=2[CH:14]=[O:15])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 27769502,3,5-TrifluorobenzaldehydeHCID 35305721-Tert-butylpiperazineHCID 22728543Water ethylacetate

Produkt 1

HCID 577743862-(4-Tert-butylpiperazin-1-yl)-3,5-difluorobenzaldehydeAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1-tert-Butylpiperazine (2.3 g, 16.2 mmol) and 2,3,5-trifluorobenzaldehyde (2.6 g, 16.2 mmol) were combined in dioxane and heated to 80° C. overnight. The yellow suspension was poured into H2O/ethyl acetate and the organic layer extracted with 1N HCl. The acidic extract was neutralized with 6N NaOH and extracted with ethyl acetate to yield the crude product as a yellow solid. This solid was purified by silica column to give 2-(4-tert-butylpiperazin-1-yl)-3,5-difluorobenzaldehyde as a yellow solid (0.96 g., 3.4 mmol, 21% yield) 1H-NMR (300 MHz, CDCl3) δ 10.52, (1H, s); 7.35 (1H, m); 7.07 (1H, m); 3.22 (4H, m); 2.71 (4H, m); 1.12 (9H, s) ppm.

Aufarbeitung

  1. extractionthe organic layer extracted with 1N HCl
  2. extractionThe acidic extract
  3. extractionextracted with ethyl acetate
  4. customto yield the crude product as a yellow solid
  5. customThis solid was purified by silica column

Quellen und Nachweise

ORD-Eintrag
ord-e47b4d1178c74676b5fc884f3b91b4aa
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163737B2

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