Water → HCID 21830850, Verbindung

HRID 1600834Notizen

Reaktionsgleichung

[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:19][CH3:20])CC)C.C([CH:23]([C:27](Cl)=[O:28])[C:24](Cl)=[O:25])C.[OH2:30]>ClCCl.C(OCC)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:27](=[O:28])[CH2:23][C:24]([O:25][CH2:19][CH3:20])=[O:30])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: -20 °C

Versuchsvorschrift

To a cooled (-20° C.) and stirred solution of N-benzylpiperazine (10 g, 56.7 mmol) and triethylamine (8.7 ml, 62.4 mmol) in dichloromethane (200 ml) was added ethyl malonyl chloride (8.5 ml, 66.4 mmol) over 10 minutes, under nitrogen. The mixture was allowed to warm to room temperature and it was stirred for 1 hour before water (100 ml) and diethyl ether (500 ml) were added. The organic phase was decanted off, washed with water (1×70 ml), 10% aqueous sodium bicarbonate (1×75 ml), brine (1×75 ml), then dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel, ethyl acetate-ethanol, 95:5) afforded 9.53 g (58%) of the title compound as a colourless oil; δH (360 MHz, CDCl3), 1.28 (3H, t, J=7.2 Hz), 2.48 (4H, br s), 3.45 (2H, s), 3.47 (2H, br s), 3.56 (2H, br s), 3.68 (2H, br s), 4.19 (2H, q, J=7.2 Hz), 7.24-7.36 (5H, m); m/e (ES) 291 (M+ +1).

Aufarbeitung

temperatureto warm to room temperature
additionwere added
customThe organic phase was decanted off
washwashed with water (1×70 ml), 10% aqueous sodium bicarbonate (1×75 ml), brine (1×75 ml)
dry with materialdried (MgSO4)
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-9353ecd8cd214f1c930644a24627c4f0
Quelldatensatz: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05977116

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