Dichloroacetyl chloride → HCID 20133039, compound

HRID 844956Notes

Reaction equation

HRID 844956 reaction equation
CC1C=CC(CCN)=CC=1.C(Cl)(=O)CC.[CH2:16]([CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([CH3:28])[CH:26]=2)[CH2:21][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]>C(Cl)Cl>[Cl:41][CH:42]([Cl:46])[C:43]([N:19]1[CH2:20][CH2:21][C:22]2[C:27](=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[CH:18]1[CH2:16][CH3:17])=[O:44]

Participants

8

Reactant 6

HCID 6593Dichloroacetyl chlorideHCID 8405IsoquinolineHCID 14798Sodium Hydroxide2×HCID 62324Propionyl chlorideHCID 76751p-MethylphenethylamineHCID 20133040HCID 20133040, compound

Product 1

HCID 20133039HCID 20133039, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By procedures described in Example 1 (Method A), 4-methyl-phenethylamine and propionyl chloride were converted to 1-ethyl-7-methyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 3.0 g of this isoquinoline compound, 10 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 and then made alkaline with aqueous sodium hydroxide. The organic extract was dried with magnesium sulfate, stripped of solvent and subjected to Kugelrohr distillation (105° C. @ 0.1 mm Hg) to provide 4.8 g of a yellow oil product having the elemental analysis reported in Table I.

Workup

  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 (105° C. @ 0.1 mm Hg)

Sources & evidence

ORD record
ord-40d41fee77224847a15d5589ad8b8e90
Source dataset
uspto-grants-1988_07
Patent number
US04755218

Reaction notes

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