Phenethylamine → HCID 20133037, compound

HRID 844951Notes

Reaction equation

HRID 844951 reaction equation
C(N)CC1C=CC=CC=1.FC(F)(F)C(Cl)=O.[F:17][C:18]([F:30])([F:29])[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][NH:20]1.C1C2C(=CC=CC=2)C=CN=1.[OH-].[Na+].[Cl:43][CH:44]([Cl:48])[C:45](Cl)=[O:46]>O.C(Cl)Cl>[Cl:43][CH:44]([Cl:48])[C:45]([N:20]1[CH2:21][CH2:22][C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]1[C:18]([F:17])([F:29])[F:30])=[O:46]

Participants

9

Reactant 6

HCID 1001PhenethylamineHCID 6593Dichloroacetyl chlorideHCID 8405IsoquinolineHCID 14798Sodium HydroxideHCID 61106Trifluoroacetyl chlorideHCID 21476433113721-77-0

Product 1

HCID 20133037HCID 20133037, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

By procedures described in Example 1 (Method A), phenethylamine and trifluoroacetyl chloride were converted to 1-trifluoromethyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 3.5 g of this isoquinoline compound, 20 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 2 minutes, then water was added. The organic extract was dried with magnesium sulfate, stripped of solvent, and subjected to Kugelrohr distillation (130° C. @ 0.1 mm Hg) to provide a 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. distillationsubjected to Kugelrohr distillation (130° C. @ 0.1 mm Hg)
  5. customto provide a product

Sources & evidence

ORD record
ord-5ce56d7639d64677b75a570b2da00412
Source dataset
uspto-grants-1988_07
Patent number
US04755218

Reaction notes

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