Potassium Carbonate → (S)-tert-butyl 4-(4-cyanophenyl)-2-methylpiperazine-1-carboxylate

HRID 69688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69688
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].F[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CC(=O)OCC>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([N:6]2[CH2:5][CH2:4][N:3]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[C@@H:2]([CH3:1])[CH2:7]2)=[CH:17][CH:18]=1)#[N:21]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylate

Produkt 1

HCID 58324511(S)-tert-butyl 4-(4-cyanophenyl)-2-methylpiperazine-1-carboxylateAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

(S)-tert-butyl 2-methylpiperazine-1-carboxylate (1 g, 4.99 mmol), 4-fluorobenzonitrile (0.605 g, 4.99 mmol), and K2CO3 (0.897 g, 6.49 mmol) were combined into a vial equipped with a stir bar. The reaction was heated to 110° C. for 48 h. Cooled to RT, diluted with EA and filtered. Concentrated to a clear oil and purified on silica gel (80 g, 10-20% EA in Hex) to give a clear oil (450 mg, 30% yield) which became a crystalline solid upon sitting. [M+H] calc'd for C17H23N3O2, 301; found, 301.

Aufarbeitung

  1. customa vial equipped with a stir bar
  2. temperatureCooled to RT
  3. filtrationfiltered
  4. concentrationConcentrated to a clear oil
  5. custompurified on silica gel (80 g, 10-20% EA in Hex)

Quellen und Nachweise

ORD-Eintrag
ord-889aa208a12844829a3e24e638b7a825
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822470B2

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