Dichloroacetyl chloride → HCID 20133046, compound

HRID 844949Notes

Reaction equation

HRID 844949 reaction equation
CC(C1C=CC=CC=1)CN.C(Cl)(=O)CC.[CH2:16]([CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]([CH3:28])[CH2:20][NH:19]1)[CH3:17].C1C2C(=CC=CC=2)C=CN=1.[OH-].[Na+].[Cl:41][CH:42]([Cl:46])[C:43](Cl)=[O:44]>O.C(Cl)Cl>[Cl:41][CH:42]([Cl:46])[C:43]([N:19]1[CH2:20][CH:21]([CH3:28])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]1[CH2:16][CH3:17])=[O:44]

Participants

9

Reactant 6

HCID 6593Dichloroacetyl chlorideHCID 8405IsoquinolineHCID 113982-PhenylpropylamineHCID 14798Sodium HydroxideHCID 62324Propionyl chlorideHCID 13143605HCID 13143605, compound

Product 1

HCID 20133046HCID 20133046, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

By procedures described in Example 1 (Method A), β-methyl-phenethylamine and propionyl chloride were converted to 1-ethyl-4-methyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 8 g of this isoquinoline compound, 10 ml 10% sodium hydroxide and 50 ml methylene chloride. With this mixture stirred, 1.1 equivalents dichloroacetyl chloride was added dropwise to the mixture. The mixture was stirred for 2 minutes, then water was added. The organic extract was dried with magnesium sulfate and stripped solvent. The residue was recrystallized from cyclohexane to provide 4 g of a white solid product having the elemental analysis reported in Table I.

Workup

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

Sources & evidence

ORD record
ord-325f9528d0244277a7d2cb2a5fbd958a
Source dataset
uspto-grants-1988_07
Patent number
US04755218

Reaction notes

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