Hydrochloric Acid → 3-(4-Aminophenyl)-4-ethylpiperazin-2-one

HRID 1363509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1363509
[CH2:1]([N:3]1[CH2:8][CH2:7][NH:6][C:5](=[O:9])[CH:4]1[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)[CH3:2].Cl.C(=O)([O-])[O-].[K+].[K+]>[Fe].C(O)C>[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH:4]2[N:3]([CH2:1][CH3:2])[CH2:8][CH2:7][NH:6][C:5]2=[O:9])=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 57625097HCID 57625097, Verbindung

Produkt 1

HCID 576251673-(4-Aminophenyl)-4-ethylpiperazin-2-oneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A 25-mL single-neck round-bottomed flask equipped with a reflux condenser and magnetic stirrer was purged with nitrogen and charged with 32 (210 mg, 0.89 mmol), ethanol (6 mL), iron powder (−325 mesh, 491 mg, 8.93 mmol) and 2N hydrochloric acid (0.70 mL, 1.40 mmol), and the mixture was heated at reflux for 30 min. After this time, the reaction was cooled to room temperature, and powdered potassium carbonate (3.03 g, 22.0 mmol) was added. The resulting suspension was filtered and the filter cake washed with ethanol (4×10 mL). The filtrate was concentrated under reduced pressure to afford 33 in 100% yield (185 mg) as a white solid: mp 153-154° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.74 (d, 1H, J=2.7 Hz), 6.90 (d, 2H, J=8.4 Hz), 6.47 (d, 2H, J=8.4 Hz), 4.95 (bs, 2H), 3.45 (m, 1H), 3.42 (s, 1H), 3.14 (m, 1H), 2.89 (m, 1H), 2.44 (m, 1H), 2.02 (s, 3H); MS (ESI+) m/z 206 (M+H).

Aufarbeitung

  1. customA 25-mL single-neck round-bottomed flask equipped with a reflux condenser and magnetic stirrer
  2. customwas purged with nitrogen
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 30 min
  5. filtrationThe resulting suspension was filtered
  6. washthe filter cake washed with ethanol (4×10 mL)
  7. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8b4906595d334a318388048caf217b28
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884108B2

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