2-Bromo-1-(3-nitrophenyl)ethan-1-one → Ethyl 1-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate

HRID 1028146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1028146
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=O.[C:14]([N:17]1[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]1)(=[S:16])[NH2:15]>C(O)C>[N+:11]([C:7]1[CH:6]=[C:5]([C:3]2[N:15]=[C:14]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]3)[S:16][CH:2]=2)[CH:10]=[CH:9][CH:8]=1)([O-:13])=[O:12]

Komponenten

4

Edukt 2

HCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 23076419Ethyl 1-carbamothioylpiperidine-4-carboxylate

Produkt 1

HCID 71075037Ethyl 1-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylateAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-bromo-1-(3-nitrophenyl)ethanone (621 mg, 2.54 mmol) and ethyl 1-carbamothioylpiperidine-4-carboxylate (500 mg, 2.31 mmol) in ethanol (7.7 mL) was heated to reflux for 16 hours, and then cooled to room temperature. The mixture was concentrated under reduced pressure and the resulting residue purified directly by CombiFlash (0-70% ethyl acetate/hexanes) to provide 457 mg (1.26 mmol, 49% yield) of ethyl 1-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate as a yellow solid.

Aufarbeitung

  1. temperatureto reflux for 16 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe resulting residue purified directly by CombiFlash (0-70% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a514779c524146dab3ad63b0f32f9037
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735417B2

Notizen zur Reaktion

Wird geladen…