Potassium Carbonate → Tert-butyl 4-(4-chloro-1,2,5-thiadiazol-3-yl)piperazine-1-carboxylate

HRID 493353

Reaktionsgleichung

Reaktionsgleichung von HRID 493353
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])([O-])=O.[K+].[K+].[Cl:20][C:21]1[C:25](Cl)=[N:24][S:23][N:22]=1>CC#N.CCOC(C)=O.O>[Cl:20][C:21]1[C:25]([N:11]2[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]2)=[N:24][S:23][N:22]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 798043,4-Dichloro-1,2,5-thiadiazoleHCID 143452tert-Butyl piperazine-1-carboxylate

Produkt 1

HCID 15524001Tert-butyl 4-(4-chloro-1,2,5-thiadiazol-3-yl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of N-Boc-piperazine (2.97 g, 15.9 mmol), K2CO3 (2.20 g, 15.9 mmol) and 3,4-dichloro-1,2,5-thiadiazole (1.5 mL, 15.9 mmol) in CH3CN (30 mL) was stirred at 100° C. for 19 h and at room temperature for 4 days. The reaction mixture was then diluted with EtOAc and water. The organic phase was dried (K2CO3) and the solvent was removed under reduced pressure. The residue was purified by chromatography on two successive silica gel columns eluting with hexane/EtOAc (1:1) and (7:3), respectively. This gave 1.54 g (31%) of the title product as a yellow solid.

Aufarbeitung

  1. dry with materialThe organic phase was dried (K2CO3)
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by chromatography on two successive silica gel columns
  4. washeluting with hexane/EtOAc (1:1) and (7:3)

Quellen und Nachweise

ORD-Eintrag
ord-8357bf44236049ea948923a54d39262c
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534794B2

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