Diisopropylethylamine → Ethyl 2-(4-methyl-3-oxopiperazin-1-yl)-2-phenylacetate

HRID 404641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 404641
CCN(C(C)C)C(C)C.Cl.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][C:13]1=[O:18].Br[CH:20]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(#N)C>[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([CH:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:14][C:13]1=[O:18]

Komponenten

5

Edukt 3

HCID 81531Diisopropylethylamine2×HCID 97780Ethyl bromophenylacetateHCID 170607661-Methylpiperazin-2-one--hydrogen chloride (1/1)

Produkt 1

HCID 86688901Ethyl 2-(4-methyl-3-oxopiperazin-1-yl)-2-phenylacetateAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

DIPEA (0.52 ml, 2.96 mmol) and 1-methylpiperazin-2-one hydrochloride (0.22 g, 1.48 mmol) were sequentially added to a solution of ethyl 2-bromo-2-phenylacetate (0.22 ml, 1.23 mmol) in acetonitrile (4 ml). The reaction was stirred at room temperature for 1.5 hours. DIPEA (0.13 ml, 0.74 mmol) was added again and the reaction was stirred at room temperature overnight. The solvent was evaporated and the crude was purified by flash chromatography (DCM/Acetone=9/1) to obtain ethyl 2-(4-methyl-3-oxopiperazin-1-yl)-2-phenylacetate (256 mg, 75% yield) as a yellow oil.

Aufarbeitung

  1. stirringthe reaction was stirred at room temperature overnight
  2. customThe solvent was evaporated
  3. customthe crude was purified by flash chromatography (DCM/Acetone=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-f849d05d494e406c90618584cd5db001
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748613B2

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