Hydrochloric Acid → Piperazine, 1-[4-bromo-2-(1,1-dimethylethyl)phenyl]-, hydrochloride (1:2)

HRID 534822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 534822
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=1.[ClH:13].[Cl:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19]Cl.[OH-].[Na+].Cl>COCCOCCOC.C(OCC)(=O)C.CCOCC>[ClH:14].[ClH:13].[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 119590004-bromo-2-tert-butylphenylamine

Produkt 1

HCID 66751142Piperazine, 1-[4-bromo-2-(1,1-dimethylethyl)phenyl]-, hydrochloride (1:2)Ausbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8150DiglymeLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A suspension of 4-bromo-2-tert-butylaniline (Reference Example 8, 25.0 g, 110 mmol) and bis(2-chloroethyl)amine hydrochloride (21.5 g, 120 mmol) in diethylene glycol dimethyl ether (157 mL) was stirred for 3 days at 170° C. It was cooled to room temperature, added 1 M sodium hydroxide solution (50 mL), and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give crude product. It was diluted with ethyl acetate and ether (50:50) and added 1 M hydrochloric acid solution to provide 1-(4-bromo-2-tert-butylphenyl)piperazine dihydrochloride (16.2 g, 40%) as a gray solid.

Aufarbeitung

  1. temperatureIt was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give crude product

Quellen und Nachweise

ORD-Eintrag
ord-aded8697d3b843e78c6180e5a9014580
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853215B2

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