4-Fluoro-2-methylaniline → 1-(4-Fluoro-2-methylphenyl)piperazine dihydrochloride

HRID 69730

Reaktionsgleichung

Reaktionsgleichung von HRID 69730
[ClH:1].[Cl:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7]Cl.[F:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[C:12]([CH3:17])[CH:11]=1>CC(O)C>[ClH:2].[ClH:1].[F:9][C:10]1[CH:16]=[CH:15][C:13]([N:14]2[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]2)=[C:12]([CH3:17])[CH:11]=1

Komponenten

4

Edukt 2

HCID 679824-Fluoro-2-methylanilineHCID 522769Bis(2-chloroethyl)amine hydrochloride

Produkt 1

HCID 184230711-(4-Fluoro-2-methylphenyl)piperazine dihydrochlorideAusbeute 5,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Bis(2-chloroethyl)amine hydrochloride (1.79 g, 10.03 mmol) and 4-fluoro-2-methylaniline (1.26 g, 10.07 mmol) were dissolved in 2-propanol (Volume: 10 mL) and stirred in a closed vial at 100° C. overnight. The reaction mixture was diluted with i-PrOH (10 mL) and cooled to 10° C. The resulting precipitate was filtered and purified using HPLC (10-80% ACN in water, TFA-buffered). The fractions were concentrated in vacuo, suspended in ether (3 mL) and treated with 4N HCl in dioxane (1 mL). The precipitate was filtered and dried in vacuum to afford 1-(4-fluoro-2-methylphenyl)piperazine dihydrochloride (150 mg, 0.561 mmol, 5.60% yield). ESI-MS: m/z 195 (M+H)+.

Aufarbeitung

  1. temperaturecooled to 10° C
  2. filtrationThe resulting precipitate was filtered
  3. custompurified
  4. concentrationThe fractions were concentrated in vacuo
  5. additiontreated with 4N HCl in dioxane (1 mL)
  6. filtrationThe precipitate was filtered
  7. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d1a58bff758f4adc97b8d733c6b1ea16
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822470B2

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