Water → 1-(2-propenyl)-4-(N-2-propylcarbamoyl)-2-piperazinone

HRID 1162809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162809
Cl.[CH2:2]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][C:6]1=[O:11])[CH:3]=[CH2:4].C(N(C(C)C)CC)(C)C.[CH3:21][CH:22]([N:24]=[C:25]=[O:26])[CH3:23].O>ClCCl>[CH2:2]([N:5]1[CH2:10][CH2:9][N:8]([C:25](=[O:26])[NH:24][CH:22]([CH3:23])[CH3:21])[CH2:7][C:6]1=[O:11])[CH:3]=[CH2:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 61277Isopropyl isocyanateHCID 81531DiisopropylethylamineHCID 684328741-(Prop-2-en-1-yl)piperazin-2-one hydrochloride

Produkt 1

HCID 684331521-(2-propenyl)-4-(N-2-propylcarbamoyl)-2-piperazinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-(2-propenyl)-2-piperazinone hydrochloride (7.9 g, 44 mmol) and diisopropylethylamine (8 mL, 46 mmol) in dichloromethane (100 mL) was added 2-propylisocyanate (5.6 g, 66 mmol). The mixture was stirred at ambient temperature for 18 h. Water (75 mL) was added, and the organic layer was collected, dried (MgSO4), filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography using a gradient elution of 2%, 3%, 4% MeOH in CH2Cl2. Product-containing fractions were combined and concentrated in vacuo to yield 1-(2-propenyl)-4-(N-2-propylcarbamoyl)-2-piperazinone as a solid. HPLC RT=2.17 min (Mehtos A); ES MS (M+H)=226; 1H NMR (400 MHz, CDCl3) δ 5.75 (ddt, 1H), 5.2 (overlapping doublets, 2H), 4.32 (b rd, 1H), 4.04 (d, J=6 Hz, 2H), 3.97 (s, 2H), 3.67 (t, J=7 Hz, 2H), 3.33 (t, J=7 hz, 2H), 1.16 (d, J=7 Hz, 6H).

Aufarbeitung

  1. customthe organic layer was collected
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by silica gel column chromatography
  6. washa gradient elution of 2%, 3%, 4% MeOH in CH2Cl2
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6cf01c19b9664c7993a6dc78b5c9cd09
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820680B2

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