Hydrochloric Acid → 2-Amino-4-{4-[2-phenoxy-ethoxy]-phenyl}-2-ethoxy-butan-1-ol hydrochloride

HRID 1865141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1865141
CC1OC[C:5]([CH2:25][OH:26])([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)[N:6]=1.[ClH:27].[CH2:28]([OH:30])[CH3:29]>>[ClH:27].[NH2:6][C:5]([O:30][CH2:28][CH3:29])([CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:13][CH:14]=1)[CH2:25][OH:26]

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 66768401(2-Methyl-4-{2-[4-(2-phenoxy-ethoxy)phenyl]-ethyl}-4,5-dihydro-oxazol-4-yl)-methanol

Produkt 1

HCID 667683972-Amino-4-{4-[2-phenoxy-ethoxy]-phenyl}-2-ethoxy-butan-1-ol hydrochloride

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 4-[2-(4-hydroxymethyl-2-methyl-4,5-dihydro-oxazol-4-yl)-ethyl]-phenol (300 mg, 1.27 mmol) in DMF (5 ml) was added Cs2CO3 (1.2 g, 3.83 mmol) and 2-phenoxyethyl bromide (770 mg, 1.27 mmol). The reaction mixture was stirred at 85° C. for 4 hours. AcOEt and water were then added, the organic layer was separated and the aqueous phase was extracted with AcOEt (3×50 ml). The combined organic extracts were washed with brine, dried over MgSO4, and evaporated to dryness. Purification by flash chromatography (AcOEt/Hx 9:1) afforded (2-Methyl-4-{2-[4-(2-phenoxy-ethoxy)phenyl]-ethyl}-4,5-dihydro-oxazol-4-yl)-methanol as colorless oil. To a solution of (2-methyl-4-{2-[4-(2-phenoxy-ethoxy)phenyl]-ethyl}-4,5-dihydro-oxazol-4-yl)-methanol (50 mg, 0.14 mmol) in ethanol (2 ml) was added conc. HCl (2 ml). The reaction mixture was stirred at 85° C. for 2 hours, then concentrated to dryness. The residue was re-dissolved in AcOEt and precipitated with hexanes. The solid was filtered off, washed with dry ether and dried in vacuo to afford 2-amino-4-{4-[2-phenoxy-ethoxy]-phenyl}-2-ethoxy-butan-1-ol hydrochloride as a colorless powder. ESI+MS: m/z=332.3 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was re-dissolved in AcOEt
  3. customprecipitated with hexanes
  4. filtrationThe solid was filtered off
  5. washwashed with dry ether
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a2acc95a2ab64ac1b5a141444cec0240
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625950B2

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