1,5-Dibromopentane → 3-Ethyl-4-(1-piperidinyl)benzonitrile
Reaktionsgleichung
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][CH3:11].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:10]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[N:1]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[C:6]#[N:7])[CH3:11]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 160 °C
Versuchsvorschrift
4-Amino-3-ethylbenzonitrile (3.0 g, 20.5 mmol), 1,5-dibromopentane (11.1 mL, 82.1 mmol), potassium carbonate (5.67 g, 41.0 mmol) and water (39.6 mL) were all split equally between ten microwave vials and each heated at 160° C. for 1 h. All the reaction mixtures were combined and extracted twice with ethyl acetate (40 mL) and the combined organic fractions dried (phase separator) and concentrated in vacuo. Dichloromethane was added, the mixture filtered and then the filtrate was purified by silica chromatography, eluting with 2-5% ethyl acetate in hexane to give the title compound as a colourless oil (823 mg, 3.85 mmol). Analysis indicated that the compound contained small amounts of a dibromopentane impurity. MS (ES): C14H18N2 requires 214; found 215 (MH+).
Aufarbeitung
- customall split equally between ten microwave vials
- customAll the reaction mixtures
- extractionextracted twice with ethyl acetate (40 mL)
- customthe combined organic fractions dried (phase separator)
- concentrationconcentrated in vacuo
- additionDichloromethane was added
- filtrationthe mixture filtered
- customthe filtrate was purified by silica chromatography
- washeluting with 2-5% ethyl acetate in hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-2bd8d369b7904e28842606bb740d0a4b
- Quelldatensatz
- uspto-grants-2012_12
- Patentnummer
- US08324254B2
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