Dichloroacetyl chloride → 2-(Dichloroacetyl)-1,4,4-trimethyl-1,2,3,4-tetrahydroisoquinoline

HRID 844957

Reaktionsgleichung

Reaktionsgleichung von HRID 844957
ClCC(C)(C1C=CC=CC=1)C.[CH3:12][CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH3:24])([CH3:23])[CH2:15][NH:14]1.C1C2C(=CC=CC=2)C=CN=1.[Cl:35][CH:36]([Cl:40])[C:37](Cl)=[O:38].[OH-].[Na+]>C(Cl)Cl.C(#N)C>[Cl:35][CH:36]([Cl:40])[C:37]([N:14]1[CH2:15][C:16]([CH3:23])([CH3:24])[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]1[CH3:12])=[O:38]

Komponenten

8

Edukt 5

HCID 6593Dichloroacetyl chlorideHCID 8405IsoquinolineHCID 14798Sodium HydroxideHCID 68191Neophyl chlorideHCID 201330451-Methyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 201330522-(Dichloroacetyl)-1,4,4-trimethyl-1,2,3,4-tetrahydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

By procedures described in Example 1 (Method B), 1-chloro-2-methyl-2-phenyl-propane and acetonitrile were converted to 1-methyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 4.0 g of this isoquinoline compound and 50 ml methylene chloride. With this mixture stirred, 2 ml dichloroacetyl chloride was added dropwise to the mixture. The mixture was stirred for 20 minutes and then made alkaline with aqueous sodium hydroxide. The organic extract was dried with magnesium sulfate and stripped of solvent. The residue was recrystallized from ethanol to provide 4.2 g of a white cubic-crystal product having the elemental analysis reported in Table I.

Aufarbeitung

  1. stirringThe mixture was stirred for 20 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-3dd54f69b57a40fb9d1c7e7449ac6457
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04755218

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