Triethylamine → 1-(4-Methoxy-2-nitrobenzyl)-4-methylpiperazine

HRID 1914677

Reaktionsgleichung

Reaktionsgleichung von HRID 1914677
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CCN(CC)CC.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[N+:25]([O-:27])=[O:26]>C(Cl)Cl.O>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[C:18]([N+:25]([O-:27])=[O:26])[CH:19]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 37478301-(Bromomethyl)-4-methoxy-2-nitrobenzene

Produkt 1

HCID 593530491-(4-Methoxy-2-nitrobenzyl)-4-methylpiperazineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-methyl piperazine (5.7 g; 57 mmol; 2 eq) in dry DCM (150 mL) are added Et3N (5.75 g; 57 mmol; 2 eq) and 1-(bromomethyl)-4-methoxy-2-nitrobenzene (7 g; 28.5 mmol; 1 eq). The mixture is stirred at room temperature for 8 h then diluted with water (150 mL). The organic phase is washed with brine and dried. The solvent is removed under vacuum to afford 6.5 g (86%) of the title compound as a viscous liquid. 1H NMR (CDCl3, 400 MHz) δ 7.46-7.44 (m, 1H), 7.34 (s, 1H), 7.08-7.05 (m, 1H), 3.86 (s, 3H), 3.73 (s, 2H), 2.54-2.46 (very br s, 8H), 2.29 (s, 3H). LC/MS (ES+): 266.0.

Aufarbeitung

  1. washThe organic phase is washed with brine
  2. customdried
  3. customThe solvent is removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-35d641163d204e2a873afce5fd572b84
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614215B2

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