Dichloroacetyl chloride → HCID 14555100, compound

HRID 231396Notes

Reaction equation

HRID 231396 reaction equation
C(C(Cl)CC1C=CC=CC=1)C.[CH3:12][CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH:15]([CH2:23][CH3:24])[NH:14]1.C1C2C(=CC=CC=2)C=CN=1.[OH-].[Na+].[Cl:37][CH:38]([Cl:42])[C:39](Cl)=[O:40]>O.C(Cl)Cl.C(#N)C>[Cl:37][CH:38]([Cl:42])[C:39]([N:14]1[CH:15]([CH2:23][CH3:24])[CH2:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]1[CH3:12])=[O:40]

Participants

9

Reactant 5

HCID 6593Dichloroacetyl chlorideHCID 8405IsoquinolineHCID 14798Sodium HydroxideHCID 524343HCID 524343, compoundHCID 13143615HCID 13143615, compound

Product 1

HCID 14555100HCID 14555100, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

By procedures described in Example 1, α-ethylphenethyl chloride and acetonitrile were converted to 1-methyl-3-ethyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 3 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 15 minutes, then water was added. The organic extract was dried with magnesium sulfate, stripped of solvent and chromatographed. A yellow oil product was recovered having the following elemental analysis:

Workup

  1. stirringThe mixture was stirred for 15 minutes
  2. extractionThe organic extract
  3. dry with materialwas dried with magnesium sulfate
  4. customchromatographed
  5. customA yellow oil product was recovered

Sources & evidence

ORD record
ord-6cbe85a9d1b044adbb44a2929e8b133f
Source dataset
uspto-grants-1989_07
Patent number
US04846880

Reaction notes

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