Piperazine → 4-(Piperazin-1-yl)thieno[3,2-c]pyridine

HRID 653407

Reaktionsgleichung

Reaktionsgleichung von HRID 653407
Cl[C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>C(O)C>[N:11]1([C:2]2[C:7]3[CH:8]=[CH:9][S:10][C:6]=3[CH:5]=[CH:4][N:3]=2)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Komponenten

4

Edukt 2

HCID 4837PiperazineHCID 128273124-Chlorothieno[3,2-c]pyridine

Produkt 1

HCID 109660274-(Piperazin-1-yl)thieno[3,2-c]pyridineAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4-chlorothieno[3,2-c]pyridine (22.7 g, 0.13 mole) and piperazine (57.7 g, 0.67 mole) were heated in a bomb with a minimum amount of ethanol (50 mL) at 120° for 24 hours. The reaction was cooled, partitioned between dichloromethane and water, and the organic layer was isolated, dried (MgSO4), filtered, and concentrated in vacuo to an oil. Flash chromatography (methylene chloride-10% methanol-1% ammonium hydroxide) of this material gave 16 g (54%) of a golden oil. Treatment of an ethanol solution of the oil with ethanolic HCl followed by recrystallization from ethanol gave the hydrochloride salt as off-white crystals, m.p. 275°-283°.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. custompartitioned between dichloromethane and water
  3. customthe organic layer was isolated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to an oil

Quellen und Nachweise

ORD-Eintrag
ord-835e7b028b934112bcad12d39be926bf
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04677104

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