Acetonitrile → 2-Amino-4-[(1,1-dimethyl)ethyl]-5-piperidinothiazole

HRID 2384471

Reaktionsgleichung

Reaktionsgleichung von HRID 2384471
[NH2:1][C:2]1[S:3][C:4](Br)=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:6]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[NH2:1][C:2]1[S:3][C:4]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:6]=1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 7291355-Bromo-4-tert-butyl-1,3-thiazol-2-amine

Produkt 1

HCID 858234922-Amino-4-[(1,1-dimethyl)ethyl]-5-piperidinothiazoleAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-amino-5-bromo-4-[(1,1-dimethyl)ethyl]thiazole (0.10 g, 0.42 mmol), piperidine (0.1 mL), potassium carbonate (0.20 g) and acetonitrile (4 mL) was refluxed for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give the title compound (80.7 mg, 79.3%) as a yellow crystal.

Aufarbeitung

  1. temperaturewas refluxed for 3 hours
  2. extractionextracted with ethyl acetate
  3. washAfter the organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe residue obtained by evaporation under reduced pressure
  6. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-06855a55e5f84de4a0df4c567e07989c
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263657B2

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