Phenethylamine → 2-(Dichloroacetyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

HRID 844952

Reaktionsgleichung

Reaktionsgleichung von HRID 844952
C(N)CC1C=CC=CC=1.C(Cl)(=O)C1C=CC=CC=1.[C:19]1([CH:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27][NH:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1C2C(=CC=CC=2)C=CN=1.[OH-].[Na+].[Cl:47][CH:48]([Cl:52])[C:49](Cl)=[O:50]>O.C(Cl)Cl>[Cl:47][CH:48]([Cl:52])[C:49]([N:26]1[CH2:27][CH2:28][C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:25]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:50]

Komponenten

9

Edukt 6

HCID 1001PhenethylamineHCID 6593Dichloroacetyl chlorideHCID 7412Benzoyl chlorideHCID 8405IsoquinolineHCID 14798Sodium HydroxideHCID 1001371,2,3,4-Tetrahydro-1-phenylisoquinoline

Produkt 1

HCID 201330332-(Dichloroacetyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

By procedures described in Example 1 (Method A), phenethylamine and benzoyl chloride were converted to 1-phenyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 3.5 g of this isoquinoline compound, 10 ml 10% sodium hydroxide and 50 ml methylene chloride. With this mixture stirred, 1.2 ml dichloroacetyl chloride was added dropwise to the mixture. The mixture was stirred for 10 minutes, then water was added. The organic extract was dried with magnesium sulfate and stripped of solvent. The residue was recrystallized from ethanol to provide 4 g of a white cubic-crystal product having the elemental analysis reported in Table I.

Aufarbeitung

  1. stirringThe mixture was stirred for 10 minutes
  2. extractionThe organic extract
  3. dry with materialwas dried with magnesium sulfate
  4. customThe residue was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-12abee4c4ac9483ca98270db7029d4fa
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04755218

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