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

HRID 844957

Reaction equation

HRID 844957 reaction equation
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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3dd54f69b57a40fb9d1c7e7449ac6457
Source dataset
uspto-grants-1988_07
Patent number
US04755218

Linked notes

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