Methyl iodide → 3-(4-Bromo-phenyl)-1-methyl-piperazine

HRID 1802776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802776
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][NH:12][CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.[CH2:14](N(CC)CC)C.CI.[Cl-].[NH4+]>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[NH:9][CH2:10][CH2:11][N:12]([CH3:14])[CH2:13]2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 218386862-(4-Bromophenyl)piperazine

Produkt 1

HCID 578992273-(4-Bromo-phenyl)-1-methyl-piperazineAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cooled (0° C.) solution of 2-(4-bromophenyl)piperazine (4.07 g, 16.0 mmol) and triethylamine (17 mL, 122 mmol) in acetone (50 mL) was added a solution of methyl iodide (1.4 mL, 22 mmol) in acetone (20 mL) over 50 min and the reaction mixture was stirred at 0° C. for 15 minutes, warmed to room temperature, and stirred for 16 h. The reaction mixture was slowly treated with saturated ammonium chloride (150 mL) and extracted with ethyl acetate (200 mL×3). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash silica gel column chromatography (heptane/ethyl acetate) gave 3-(4-bromo-phenyl)-1-methyl-piperazine (1.89 g, 46% yield). LCMS (m/z): 257.00 (M+1).

Aufarbeitung

  1. temperaturewarmed to room temperature
  2. stirringstirred for 16 h
  3. extractionextracted with ethyl acetate (200 mL×3)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification via flash silica gel column chromatography (heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7be4b9ce46754c03853998d73cba79e3
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349883B2

Notizen zur Reaktion

Wird geladen…