Ammonium Hydroxide → Ethyl 2-(piperidin-4-yl)-1,3-thiazole-5-carboxylate

HRID 715804

Reaktionsgleichung

Reaktionsgleichung von HRID 715804
C(O[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])C.BrN1C(=O)CCC1=O.[C:19]([CH:22]1[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]1)(=[S:21])[NH2:20].[OH-].[NH4+]>O1CCOCC1.O>[NH:25]1[CH2:26][CH2:27][CH:22]([C:19]2[S:21][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:20]=2)[CH2:23][CH2:24]1

Komponenten

6

Edukt 4

HCID 14923Ammonium HydroxideHCID 67184N-bromobutanimideHCID 221780Ethyl 3-ethoxy-2-propenoateHCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylate

Produkt 1

HCID 86701983Ethyl 2-(piperidin-4-yl)-1,3-thiazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

Ethyl 3-ethoxyacrylate (1.50 g, 10.38 mml) was dissolved in dioxane/water and chilled to −10° C. N-Bromosuccinimide (2.03 g, 11.42 mmol) was added and the mixture was stirred 1 hour at room temperature. tert-Butyl 4-carbamothioylpiperidine-1-carboxylate (2.54 g, 10.38 mmol) was added and the mixture was heated at 100° C. for 1 hour. The reaction mixture was poured into 25 mL saturated ammonium hydroxide and extracted with dichloromethane. The combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. Normal phase chromatography provided the title compound.

Aufarbeitung

  1. temperaturethe mixture was heated at 100° C. for 1 hour
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-329f3457c78540efbaeee55cee310da5
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187472B2

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