Sodium Iodide → 1-Acetyl-4-[2-(4-nitrophenoxy)ethyl]piperazine

HRID 1656598Notizen

Reaktionsgleichung

[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[N+:10]([C:13]1[CH:22]=[CH:21][C:16]([O:17][CH2:18][CH2:19]Br)=[CH:15][CH:14]=1)([O-:12])=[O:11].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:19][CH2:18][O:17][C:16]2[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:22][CH:21]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

To a stirring solution of N-acetylpiperazine (5.10 g, 40.0 mmol) in acetonitrile (100 mL) was added 1-(4-nitrophenoxy)-2-bromoethane (10.0 g, 40.0 mmol), K2CO3 (15 g, 108 mmol), and NaI (0.90 g, 6.0 mmol). The mixture was stirred under nitrogen at 70° C. for 24 hours, cooled, and concentrated. The residue was partitioned between ethyl acetate/10% aqueous K2CO3. The organic phase was dried and concentrated to afford crude product which was purified by flash column chromatography (5% CH3OH/CH2Cl2) to afford 7.07 g (61%) of 1-acetyl-4-[2-(4-nitrophenoxy)ethyl]piperazine as a semisolid: 1H NMR (CDCl3): δ 8.20 (d, J=9.6 Hz, 2H), 6.95 (d, J=9.6 Hz, 2 h), 4.20 (t, J=6.0 Hz, 2H), 3.65 (m, 2 H), 3.50 (m, 2H), 2.85 (t, J=6.0 Hz, 2H), 2.55 (m, 6H), 2.08 (s, 3H).

Aufarbeitung

temperaturecooled
concentrationconcentrated
customThe residue was partitioned between ethyl acetate/10% aqueous K2CO3
customThe organic phase was dried
concentrationconcentrated
customto afford crude product which
customwas purified by flash column chromatography (5% CH3OH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag: ord-5621d2effbce4c9b8478beefcb48814b
Quelldatensatz: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05254689

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