Dichloroacetyl chloride → HCID 14555099, compound

HRID 231395Notes

Reaction equation

HRID 231395 reaction equation
CC(Cl)CC1C=CC=CC=1.C(#N)CC.[CH2:15]([CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH:19]([CH3:27])[NH:18]1)[CH3:16].C1C2C(=CC=CC=2)C=CN=1.[OH-].[Na+].[Cl:40][CH:41]([Cl:45])[C:42](Cl)=[O:43]>O.C(Cl)Cl>[Cl:40][CH:41]([Cl:45])[C:42]([N:18]1[CH:19]([CH3:27])[CH2:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:17]1[CH2:15][CH3:16])=[O:43]

Participants

9

Reactant 6

HCID 6593Dichloroacetyl chlorideHCID 7854PropionitrileHCID 8405IsoquinolineHCID 14798Sodium HydroxideHCID 231365(2-Chloropropyl)benzeneHCID 20032343HCID 20032343, compound

Product 1

HCID 14555099HCID 14555099, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

By procedures described in Example 1, α-methylphenethylchloride and propionitrile were converted to 1-ethyl-3-methyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 4 g of this isoquinoline compound, 10 ml 10% sodium hydroxide and 50 ml methylene chloride. With this mixture stirred, 1.1 equivalents dichloro-acetyl 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 aulfate, and stripped of solvent, and subjected to Kugelrohr distillation (150° C. @0.25 mm Hg) to provide 4.5 g of a yellow oil product 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 aulfate
  4. distillationsubjected to Kugelrohr distillation (150° C. @0.25 mm Hg)

Sources & evidence

ORD record
ord-3381c95c3ffe4ab7a5d9b5733a96a176
Source dataset
uspto-grants-1989_07
Patent number
US04846880

Reaction notes

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