Sodium Azide → Tert-butyl 4-(3-azidopropyl)piperazine-1-carboxylate

HRID 1618811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1618811
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16]Cl)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:18]=[N+:19]=[N-:20].[Na+]>CS(C)=O>[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:18]=[N+:19]=[N-:20])[CH2:10][CH2:9]1)([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 53412057tert-Butyl 4-(3-chloropropyl)piperazine-1-carboxylate

Produkt 1

HCID 86625340Tert-butyl 4-(3-azidopropyl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Tert-Butyl-4-(3-Chloropropyl)-1-piperazine carboxylate and sodium-azide were dissolved (suspended) in 8 ml DMSO dry and heated to 90° C. for 15 h. The reaction mixture was allowed to cool to room temperature and pored into 50 ml of water. The product was extracted with DCM and the combined organic phases dried over MgSO4. The product was purified by flash column chromatography (n-heptane/ethylacetate 1:1, RF=0.34). Yield: 3.5 g.

Aufarbeitung

  1. customdry
  2. temperatureto cool to room temperature
  3. extractionThe product was extracted with DCM
  4. dry with materialthe combined organic phases dried over MgSO4
  5. customThe product was purified by flash column chromatography (n-heptane/ethylacetate 1:1, RF=0.34)

Quellen und Nachweise

ORD-Eintrag
ord-8b0799e26f6f48afbf58aa32af44d541
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08771644B2

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