Hydrogen Bromide → 3-(Furan-2-yl)-acryloylpiperazine

HRID 1449156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1449156
O.O.O.O.O.O.[NH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.Br.[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH:19]=[CH:20][C:21](Cl)=[O:22].Cl>O1CCCC1.C(O)C>[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH:19]=[CH:20][C:21]([N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:22]

Komponenten

7

Edukt 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 120181Piperazine, hexahydrateHCID 534112853-(Furan-2-yl)prop-2-enoyl chloride

Produkt 1

HCID 537585833-(Furan-2-yl)-acryloylpiperazineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a homogeneous solution of 15.6 g. (80 mM) of piperazine hexahydrate and 13.8 g. (80 mM) of 47% hydrobromic acid in 40 ml. of ethanol there were added dropwise at room temperature another solution of 6.3 g. (40 mM) of 3-(Furan-2-yl)-acryloylchloride in 10 ml. of tetrahydrofuran. After stirring for two hours at room temperature, the resulting solution was heated at 80° for two hours. Then the solution was cooled with ice and the forming crystals of piperazine hydrobromide were filtered off. The filtrate was condensed under reduced pressure and 80 ml. of 2 N-hydrochloric acid was added into the residue. After neutral substances were removed by extraction with ethyl acetate, the resulting solution was made alkaline with 5 N sodium hydroxide and extracted again with ethyl acetate. After drying over anhydrous sulfate, the combined extracts were condensed to give 4.62 g. of 3-(Furan-2-yl)-acryloylpiperazine (56% yield).

Aufarbeitung

  1. temperaturethe resulting solution was heated at 80° for two hours
  2. temperatureThen the solution was cooled with ice
  3. filtrationthe forming crystals of piperazine hydrobromide were filtered off
  4. customcondensed under reduced pressure and 80 ml
  5. customAfter neutral substances were removed by extraction with ethyl acetate
  6. extractionextracted again with ethyl acetate
  7. dry with materialAfter drying over anhydrous sulfate
  8. customcondensed
  9. customto give 4.62 g

Quellen und Nachweise

ORD-Eintrag
ord-576b6ec6dc7f4a85a1217070abbbbbf7
Quelldatensatz
uspto-grants-1980_02
Patentnummer
US04189484

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