Benzaldehyde → 3-(3,4-Dimethoxyphenyl-2-propyl]-5-hydroxymethyl-2-phenyloxazolidine

HRID 1285585

Reaktionsgleichung

Reaktionsgleichung von HRID 1285585
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH:14][CH2:15][CH:16]([OH:19])[CH2:17][OH:18])[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([N:14]2[CH2:15][CH:16]([CH2:17][OH:18])[O:19][CH:20]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 243Benzoic AcidHCID 537726823-[3-(3,4-Dimethoxyphenyl)-2-propylamino]1,2-propanediol

Produkt 1

HCID 147206783-(3,4-Dimethoxyphenyl-2-propyl]-5-hydroxymethyl-2-phenyloxazolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 3-[3-(3,4-dimethoxyphenyl)-2-propylamino]-1,2-propanediol (14.3 g., 0.053 m.), benzaldehyde (12.7 g., 0.12 m.) and benzoic acid (0.3 g.) in toluene (45 ml.) is refluxed for 3 hours, collecting the water formed in a Dean-Stark trap. After washing with saturated NaHCO3 solution and with H2O (2x), the solvent is distilled under reduced pressure. Excess benzaldehyde is distilled at 100° C. at 0.1 mm. The residue, (II) (16.88 g., 89%) is used without further purification in the next step.

Aufarbeitung

  1. temperatureis refluxed for 3 hours
  2. customcollecting the water
  3. customformed in a Dean-Stark trap
  4. washAfter washing with saturated NaHCO3 solution and with H2O (2x)
  5. distillationthe solvent is distilled under reduced pressure
  6. distillationExcess benzaldehyde is distilled at 100° C. at 0.1 mm
  7. customThe residue, (II) (16.88 g., 89%) is used without further purification in the next step

Quellen und Nachweise

ORD-Eintrag
ord-12bb931e429d4511b314304f4ee81cb8
Quelldatensatz
uspto-grants-1986_01
Patentnummer
US04567276

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