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

HRID 447324

Reaktionsgleichung

Reaktionsgleichung von HRID 447324
[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-2e52ba7f18b740f483eb8c0f805e1dc4
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481533B2

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