Methyl Acrylate → HCID 86680440, Verbindung

HRID 1184578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184578
Cl.[N:2]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][CH2:6][NH:5][CH:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1.[C:19]([O:23][CH3:24])(=[O:22])[CH:20]=[CH2:21]>CO>[CH3:24][O:23][C:19](=[O:22])[CH2:20][CH2:21][N:5]1[CH2:6][CH2:7][N:2]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3][CH:4]1[C:8]([O:10][CH3:11])=[O:9]

Komponenten

4

Edukt 2

HCID 7294Methyl AcrylateHCID 450721861-Tert-butyl 3-methyl piperazine-1,3-dicarboxylate hydrochloride

Produkt 1

HCID 86680440HCID 86680440, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 1-tert-butyl 3-methyl piperazine-1,3-dicarboxylate hydrochloride, (200 g, 0.82 mol) in methanol (1 L) was added methyl acrylate (214 g, 2.46 mol) with stirring at approximately 25° C. under N2 atmosphere, and the reaction mixture was refluxed at 70° C. for 48 hours. The volatiles were removed under reduced pressure, and the residue was partitioned between ethyl acetate (1.2 L) and water (2 L). The organic layer was separated and washed with water (1 L×2) and brine (500 mL), dried over Na2SO4, filtered and concentrated. The crude obtained was purified by column chromatography over silica gel using 30-40% ethyl acetate in petroleum ether to give the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.43 (s, 9H), 2.20-2.34 (m, 1H), 2.35-2.46 (m, 1H), 2.48 (t, 2H, J=7.2 Hz), 2.76-2.90 (m, 1H), 2.90-3.12 (m, 2H), 3.12-3.30 (m, 1H), 3.32 (t, 1H, J=4.5 Hz), 3.35-3.44 (m, 1H), 3.67 (s, 3H), 3.71 (s, 3H) 3.83-3.94 (m, 1H).

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed at 70° C. for 48 hours
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was partitioned between ethyl acetate (1.2 L) and water (2 L)
  4. customThe organic layer was separated
  5. washwashed with water (1 L×2) and brine (500 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude obtained
  10. customwas purified by column chromatography over silica gel using 30-40% ethyl acetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-2b083bd6c4384cbc88d5c959ee381c57
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669255B2

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