Triethylamine → 1-(4-Bromobenzoyl)-4-methylpiperazine

HRID 1466286Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1466286
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CCN(CC)CC.[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>C(Cl)Cl>[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[O:21])=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 685154-Bromobenzoyl chloride

Produkt 1

HCID 44643521-(4-Bromobenzoyl)-4-methylpiperazineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of N-methylpiperizine (1.00 g, 10 mmol) and Et3N (2.1 mL, 15 mmol) in CH2Cl2 (50 mL) at rt was added 4-bromobenzoyl chloride (2.195 g, 10 mmol) in one portion. The reaction was heated to reflux briefly and cooled. The resulting mixture was stirred O/N at rt. The reaction was quenched with H2O (30 mL) and sat. NaHCO3 (10 mL), separated and dried (Na2SO4). Evaporation of solvents afforded the title compound as a pale yellowish white solid (2.69 g, 95%). 1H NMR (400 MHz, CDCl3) δ 7.64 (d, J=8.4 Hz, 2H), 7.33 (d, J=8.4 Hz, 2H), 3.70-3.20 (m, 4H), 2.40-2.15 (m, 7H; s, 3H at 2.18 ppm and m, 4H overlapping); MS ESI 283.0 [M+H]+, calcd. for [C12H15BrN2O+H]+ 283.0.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux briefly
  3. temperaturecooled
  4. customThe reaction was quenched with H2O (30 mL) and sat. NaHCO3 (10 mL)
  5. customseparated
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of solvents

Quellen und Nachweise

ORD-Eintrag
ord-19a76c0ffa0a4a1ab16bbaf3c0b60484
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999968B2

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