Sulfuric Acid → 1-[1-(4-Aminophenyl)-2-dimethylaminoethyl]cyclohexanol
Reaktionsgleichung
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]([N:18]([CH3:20])[CH3:19])=O)[C:9]2([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O>O1CCCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]2([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:16][N:18]([CH3:20])[CH3:19])=[CH:6][CH:7]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
5.0 g (0.018 mole) of the above amide was dissolved in 300 ml of dry tetrahydrofuran and added dropwise to a mixture of 1.1 g of lithium aluminum hydride and 8.0 ml of concentrated sulfuric acid in 200 ml of tetrahydrofuran at 0° C. The mixture was stirred at 0° C. for five hours, then the excess reagent was destroyed by the dropwise addition of 4 ml of 50:50 THF-water, then 4 ml of 15% aqueous sodium hydroxide and finally 4 ml of water. The mixture was filtered and the precipitate washed several times with THF. The combined filtrates were evaporated and the residue recrystallized from isopropanol to give 3.8 g of the title compound as the free base. Treatment with excess oxalic acid in ethyl acetate gave the dioxalate, m.p. 105° C.(d).
Aufarbeitung
- customthe excess reagent was destroyed by the dropwise addition of 4 ml of 50:50 THF-water
- filtrationThe mixture was filtered
- washthe precipitate washed several times with THF
- customThe combined filtrates were evaporated
- customthe residue recrystallized from isopropanol
Quellen und Nachweise
- ORD-Eintrag
- ord-df257a6cda8142a4a266a82264328e93
- Quelldatensatz
- uspto-grants-1988_08
- Patentnummer
- US04761501
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