1-Butanol → 1-(N-benzyloxycarbonyl-3,4,5-trimethoxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 27147

Reaktionsgleichung

Reaktionsgleichung von HRID 27147
C(O[CH:4](OCC)[CH2:5][N:6]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1)C.[ClH:32].[OH:33][C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][C:42]=1[OH:43])[CH2:37][CH2:38][NH2:39].C(O)CCC>O>[ClH:32].[CH2:22]([O:21][C:19]([N:6]([CH2:5][CH:4]1[C:40]2[C:36](=[CH:35][C:34]([OH:33])=[C:42]([OH:43])[CH:41]=2)[CH2:37][CH2:38][NH:39]1)[C:7]1[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 2631-ButanolHCID 65340Dopamine HydrochlorideHCID 20460529N-benzyloxycarbonyl-3,4,5-trimethoxyanilinoacetaldehyde diethyl acetal

Produkt 1

HCID 204605511-(N-benzyloxycarbonyl-3,4,5-trimethoxyanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

N-benzyloxycarbonyl-3,4,5-trimethoxyanilinoacetaldehyde diethyl acetal (21 g) and 3,4-dihydroxyphenethylamine hydrochloride (8.3 g) were added to a mixture of n-butyl alcohol (210 ml) and water (30 ml) and then the mixture was refluxed for 11 hours in a stream of nitrogen. In the course of the reaction, amounts of the above-mentioned acetal (2.1 g, 2.1 g and 4.2 g) were added to the mixture after 5 hours, 6 hours and 7 hours, respectively, from the beginning of the reaction, respectively. The reaction mixture was concentrated to dryness under reduced pressure and the residue was washed with ether and acetone to give 1-(N-benzyloxycarbonyl-3,4,5-trimethoxyanilinomethyl)-6,7-dihydroxy,1,2,3,4-tetrahydroisoquinoline hydrochloride (16.3 g). The product was recrystallized from a mixed solvent of ethanol and ether to give a pure product, mp 197° to 199° C. (dec).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 11 hours in a stream of nitrogen
  2. additionwere added to the mixture after 5 hours, 6 hours and 7 hours
  3. customrespectively, from the beginning of the reaction
  4. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  5. washthe residue was washed with ether and acetone

Quellen und Nachweise

ORD-Eintrag
ord-a43635fea12b4c809e92f1044b1ffa83
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04220647

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