1-Butanol → 4-(Piperazin-1-yl)benzonitrile hydrochloride

HRID 1639070

Reaktionsgleichung

Reaktionsgleichung von HRID 1639070
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].C(O)CCC.[ClH:27]>C(OCC)(=O)C>[ClH:27].[N:10]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Komponenten

7

Edukt 5

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 4837PiperazineHCID 11430Potassium CarbonateHCID 12162Benzonitrile, 4-bromo-

Produkt 1

HCID 27339944-(Piperazin-1-yl)benzonitrile hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 27.3 g (0.15 mole) of p-bromobenzonitrile, 38.7 g (0.45 mole) of piperazine and 42.0 g (0.30 mole) of solid potassium carbonate in a total volume of 60 ml of n-butanol was heated at reflux for 16 hr under a nitrogen atmosphere. The mixture was concentrated under reduced pressure and the slurry partitioned between 10% sodium hydroxide and chloroform. The chloroform layer was separated, dried over magnesium sulfate and concentrated under reduced pressure to give an oil. The oil was eluted through a 400 g silica gel column with a 10% methanol in methylene chloride mixture. The appropriate fractions were concentrated under reduced pressure to give a golden oil. Trituration of this oil with ethyl acetate gave a white powder. The collected white powder was stirred for 15 min in ethereal hydrogen chloride and recrystallized from methanol-water to give 1.5 g (4.5%)* of white solid, m.p. 160° C. with decomposition.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 16 hr under a nitrogen atmosphere
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe slurry partitioned between 10% sodium hydroxide and chloroform
  5. customThe chloroform layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil
  9. washThe oil was eluted through a 400 g silica gel column with a 10% methanol in methylene chloride mixture
  10. concentrationThe appropriate fractions were concentrated under reduced pressure
  11. customto give a golden oil
  12. customrecrystallized from methanol-water
  13. customto give 1.5 g (4.5%)* of white solid, m.p. 160° C. with decomposition

Quellen und Nachweise

ORD-Eintrag
ord-f32a01d80fc047809de585231398b386
Quelldatensatz
uspto-grants-1989_11
Patentnummer
US04882330

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