Hydrogen chloride-ethyl acetate → 2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine
Reaktionsgleichung
C(OC(=O)[NH:7][CH2:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]1[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:10])(C)(C)C.Cl.CCOC(C)=O>CCOC(C)=O>[CH:21]1([CH:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:19][CH2:20][N:11]2[C:9](=[O:10])[CH2:8][NH2:7])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
Tert-butyl[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]carbamate (1.5 g) was dissolved in EtOAc (20 mL), and 4 M HCl/EtOAc (3 mL) was added thereto under ice-cooling, followed by stirring at 50° C. for 5 hours. Then, the reaction solvent was evaporated. Saturated aqueous sodium bicarbonate was added to the reaction liquid which was then extracted with chloroform. The extract was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (chloroform-MeOH) to obtain 2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine (1.09 g).
Aufarbeitung
- temperatureunder ice-cooling
- customThen, the reaction solvent was evaporated
- additionSaturated aqueous sodium bicarbonate was added to the reaction liquid which
- extractionwas then extracted with chloroform
- washThe extract was washed with saturated brine
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated
- customthe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)
Quellen und Nachweise
- ORD-Eintrag
- ord-7a20500d789c4f14b5e2b2c6c8b218b9
- Quelldatensatz
- uspto-grants-2012_09
- Patentnummer
- US08263607B2
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