Chloroacetyl chloride → N-(1-Benzyl-piperidin-4-yl)-2-chloro-N-isopropyl-acetamide
Reaktionsgleichung
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15]([CH3:17])[CH3:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl:27][CH2:28][C:29](Cl)=[O:30]>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:15]([CH3:17])[CH3:16])[C:29](=[O:30])[CH2:28][Cl:27])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Komponenten
5
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a mixture of 1-benzyl-4-(isopropylamino)piperidine (8 g, 34.45 mmol) and DIPEA (7.2 mL, 41.3 mmol) in 200 mL of dichloromethane was added dropwise a solution of 2-chloroacetyl chloride (3.01 mL, 37.9 mmol) in dichloromethane (400 mL) at 0° C. The reaction mixture was stirred at 0° C. for 15 min and then at room temperature for 2 h. The reaction mixture was then washed with saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by flash column chromatography (ethyl acetate/hexane/triethylamine: 42.5/56.5/1) to give 5.35 g of the title intermediate as a viscous oil (50% yield).
Aufarbeitung
- waitat room temperature for 2 h
- washThe reaction mixture was then washed with saturated sodium bicarbonate, brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe resulting residue was purified by flash column chromatography (ethyl acetate/hexane/triethylamine: 42.5/56.5/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-8ad26682b0504b708107dd6c8d9b3147
- Quelldatensatz
- uspto-grants-2011_10
- Patentnummer
- US08030502B2
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