Diisopropylethylamine → 4-(3-(Trifluoromethyl)pyridin-2-yl)piperazin-2-one

HRID 912887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 912887
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].Cl[C:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:12]=[CH:11][N:10]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.O>[F:16][C:15]([F:18])([F:17])[C:14]1[C:9]([N:4]2[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]2)=[N:10][CH:11]=[CH:12][CH:13]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 231360Piperazin-2-oneHCID 5898332-Chloro-3-(trifluoromethyl)pyridine

Produkt 1

HCID 471744384-(3-(Trifluoromethyl)pyridin-2-yl)piperazin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of piperazin-2-one (4.85 g, 48.47 mmol, Avocado Research), 2-chloro-3-trifluoromethyl-pyridine (8.8 g, 48.47 mmol, TCI America) and diisopropylethylamine (111 mL, 58.16 mmol, Aldrich) in DMSO (160 mL) was heated at 120° C. for 16 h. The mixture was cooled to room temperature, diluted with H2O (500 mL) and extracted with EtOAc (2×500 mL). The combined organic extracts were dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography, eluting with dichloromethane/MeOH (15:1) to give the title compound as a yellow solid. MS (ESI, positive ion) m/z: 206 (M+1).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with EtOAc (2×500 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with dichloromethane/MeOH (15:1)

Quellen und Nachweise

ORD-Eintrag
ord-06b8b03b67ca43dd8e62875f1ded4b51
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026241B2

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