Hydrochloric Acid → 4-[2-(2-Hydroxy-2-phenylethylamino)ethoxy]phenylacetamide hydrochloride

HRID 275453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275453
C([N:8]([CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([NH2:30])=[O:29])=[CH:23][CH:22]=1)[CH2:9][CH:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C1C=CC=CC=1.CCOCC.[ClH:36]>CC(O)C.C(O)(=O)C.[Pd].C(OCC)(=O)C>[ClH:36].[OH:17][CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][NH:8][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([NH2:30])=[O:29])=[CH:23][CH:22]=1

Komponenten

8

Edukt 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 117419734-[2-(N-benzyl-N-(2-hydroxy-2-phenylethyl)amino)ethoxy]phenylacetamide

Produkt 1

HCID 189972404-[2-(2-Hydroxy-2-phenylethylamino)ethoxy]phenylacetamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A preformed solution of 4-[2-(N-benzyl-N-(2-hydroxy-2-phenylethyl)amino)ethoxy]phenylacetamide in propan-2-ol and glacial acetic acid (see below) was hydrogenated in the presence of 10% w/w palladium on carbon (1.0 g) at about 20 bar and 60° C. for 12 hours. The mixture was cooled, filtered and the filtrate was evaporated under reduced pressure. The residual oil thus obtained was dissolved in ethyl acetate and treated with a solution of ether saturated with hydrogen chloride. The precipitated solid was crystallised from methanol to give 4-[2-(2-hydroxy-2-phenylethylamino)-ethoxy]phenylacetamide hydrochloride (6.8 g), m.p. 250°-251° C. (softens at about 248° C.); microanalysis: found C, 61.2; H, 6.5; N, 8.3; Cl, 10.3%; required for C18H23ClN2O3 : C, 61.6; H, 6.6; N, 8.0; Cl, 10.1%.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residual oil thus obtained
  5. customThe precipitated solid was crystallised from methanol

Quellen und Nachweise

ORD-Eintrag
ord-37d1c04858d5451db22943e62410c7ba
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05393779

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