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

HRID 844954

Reaktionsgleichung

Reaktionsgleichung von HRID 844954
CC(C1C=CC=CC=1)CN.C(Cl)(=O)C1C=CC=CC=1.CC1C2C(=CC=CC=2)CNC1.[CH3:31][CH:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[NH:34][CH2:33]1.C1C2C(=CC=CC=2)C=CN=1.[OH-].[Na+].[Cl:60][CH:61]([Cl:65])[C:62](Cl)=[O:63]>O.C(Cl)Cl>[Cl:60][CH:61]([Cl:65])[C:62]([N:34]1[CH2:33][CH:32]([CH3:31])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]1[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:63]

Komponenten

10

Edukt 7

HCID 6593Dichloroacetyl chlorideHCID 7412Benzoyl chlorideHCID 8405IsoquinolineHCID 113982-PhenylpropylamineHCID 14798Sodium HydroxideHCID 137389344-Methyl-1,2,3,4-tetrahydroisoquinolineHCID 146126774-Methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 201330532-(Dichloroacetyl)-1-phenyl-4-methyl-1,2,3,4-tetrahydroisoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

By procedures described in Example 1 (Method A), β-methyl-phenethylamine and benzoyl chloride were converted to 4-methyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged 4-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 3.0 g of this isoquinoline compound, 5 ml 10% sodium hydroxide and 50 ml methylene chloride. With this mixture stirred, 2 ml dichloroacetyl chloride was added dropwise to the mixture. The mixture was stirred for 5 minutes, then water was added. The organic extract was dried with magnesium sulfate, stripped of solvent and subjected to Kugelrohr distillation (160° C. @ 0.1 mm Hg) to provide 4 g of a yellow oil product having the elemental analysis reported in Table I.

Aufarbeitung

  1. stirringThe mixture was stirred for 5 minutes
  2. extractionThe organic extract
  3. dry with materialwas dried with magnesium sulfate
  4. distillationsubjected to Kugelrohr distillation (160° C. @ 0.1 mm Hg)

Quellen und Nachweise

ORD-Eintrag
ord-3d0361730734420088bfd9d462db1b3d
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04755218

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