Triethylamine → alpha-[[(2,3-Dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol

HRID 1089468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1089468
Cl.[NH2:2][CH2:3][CH:4]([OH:15])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.[CH3:16][O:17][C:18]1[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=O.C(N(CC)CC)C.B.[Na]>CO>[CH3:16][O:17][C:18]1[C:25]([O:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][NH:2][CH2:3][CH:4]([OH:15])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 665812,3-DimethoxybenzaldehydeHCID 128889092-Amino-1-(3,4-dimethoxyphenyl)ethan-1-ol hydrochlorideHCID 178418435HCID 178418435, Verbindung

Produkt 1

HCID 14719553alpha-[[(2,3-Dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcoholAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1.0 g of α-(aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride was suspended in 5 ml of methanol, and after adding thereto 0.85 g of 2,3-dimethoxybenzaldehyde, 0.63 ml of triethylamine was added dropwise to the mixture while stirring at room temperature. The mixture was heated under reflux for 30 minutes, and 0.24 g of sodium boron hydride was added slowly to the mixture while stirring under ice cooling. After the foaming stopped, the mixture was concentrated. The residue was subjected to a separating procedure with chloroform and water, the chloroform layer was collected, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was recrystallized from ethyl acetate-n-hexane, giving 1.07 g of α-[[(2,3-dimethoxybenzyl)amino]methyl]-3,4-dimethoxybenzyl alcohol, m.p. 96°-97° C.

Aufarbeitung

  1. additionafter adding
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 30 minutes
  4. stirringwhile stirring under ice cooling
  5. concentrationthe mixture was concentrated
  6. customthe chloroform layer was collected
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. customthe residue was recrystallized from ethyl acetate-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-99c55bdfc17c4a498635ef1d21b7952f
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04966904

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