(1R)-2-((2-(4-Nitrophenyl)ethyl)amino)-1-phenylethan-1-ol--hydrogen chloride (1/1) → 2-((4-Aminophenethyl)amino)-1-phenylethanol hydrochloride, (R)-
Reaktionsgleichung
[ClH:1].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][CH2:14][C@@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[OH:16])=[CH:7][CH:6]=1)([O-])=O.[H][H]>[C].[Pd].CO>[ClH:1].[NH2:2][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][NH:13][CH2:14][C@@H:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[OH:16])=[CH:9][CH:10]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 20 °C
Versuchsvorschrift
A mixture of 11.0 kg of (R)-2-[[2-(4-nitrophenyl)ethyl]amino]-1-phenylethanol monohydrochloride, 110 liters of methanol and 1.20 kg of wet 10% palladium-carbon (wetting rate: 54.2%) was stirred in a hydrogen atmosphere until absorption of hydrogen stopped. The reaction solution was filtered and the filtrate was concentrated in vacuo. Methanol (40 liters) was added to the residue to dissolve at 40° C. and crystallization was conducted by addition of 220 liters of diisopropyl ether thereto followed by stirring at 20° C. throughout one night. The crystals were filtered and washed with 30 liters of diisopropyl ether. They were dried in vacuo to give 9.43 kg of (R)-2-[[2-(4-aminophenyl)ethyl]amino]-1-phenylethanol monohydrochloride.
Aufarbeitung
- filtrationThe reaction solution was filtered
- concentrationthe filtrate was concentrated in vacuo
- additionMethanol (40 liters) was added to the residue
- dissolutionto dissolve at 40° C.
- customcrystallization
- additionwas conducted by addition of 220 liters of diisopropyl ether
- filtrationThe crystals were filtered
- washwashed with 30 liters of diisopropyl ether
- customThey were dried in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-793c1d2a3abf48ef9e611660c68ae9e9
- Quelldatensatz
- uspto-grants-2014_04
- Patentnummer
- USRE044872E1
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