5-Bromothiophene-2-carbaldehyde → 5-PIPERAZIN-1-YLTHIOPHENE-2-CARBALDEHYDE

HRID 336833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336833
Br[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[N:9]1(C(OC(C)(C)C)=O)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1>O>[N:9]1([C:2]2[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=2)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

Komponenten

4

Edukt 2

HCID 784285-Bromothiophene-2-carbaldehydeHCID 143452tert-Butyl piperazine-1-carboxylate

Produkt 1

HCID 24631775-PIPERAZIN-1-YLTHIOPHENE-2-CARBALDEHYDEAusbeute 71,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A suspension of 1.09 g (5.7 mmol) of 5-bromothiophene-2-carboxaldehyde and 3.19 g (17.1 mmol) of tert-butyl piperazine-1-carboxylate in 30 ml of water is heated under reflux for 48 h. The aqueous phase is extracted three times with methylene chloride. The organic phases are combined, dried over sodium sulfate, filtered, and evaporated. The residue is purified by chromatography on silica (MeOH gradient in dichloromethane: 5 to 10%) to yield 0.80 g (70%) of 5-(piperazin-1-yl)thiophene-2-carboxaldehyde in the form of a blue-grey solid.

Aufarbeitung

  1. temperatureis heated
  2. temperatureunder reflux for 48 h
  3. extractionThe aqueous phase is extracted three times with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by chromatography on silica (MeOH gradient in dichloromethane: 5 to 10%)

Quellen und Nachweise

ORD-Eintrag
ord-5668f39988284b37ad4c806bd5df46cf
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889711B2

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