Phenethylamine → HCID 20133036, compound

HRID 844945Notes

Reaction equation

HRID 844945 reaction equation
C(N)CC1C=CC=CC=1.C(Cl)(=O)CC.[CH2:15]([CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][NH:18]1)[CH3:16].C1C2C(=CC=CC=2)C=CN=1.[Cl:37][CH:38]([Cl:42])[C:39](Cl)=[O:40]>C1(C)C=CC=CC=1>[Cl:37][CH:38]([Cl:42])[C:39]([N:18]1[CH2:19][CH2:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:17]1[CH2:15][CH3:16])=[O:40]

Participants

7

Reactant 5

HCID 1001PhenethylamineHCID 6593Dichloroacetyl chlorideHCID 8405IsoquinolineHCID 62324Propionyl chlorideHCID 3798338HCID 3798338, compound

Product 1

HCID 20133036HCID 20133036, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

By procedures described in Example 1 (Method A), phenethylamine and propionyl chloride were converted to 1-ethyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 2.5 g of this isoquinoline compound in 50 ml toluene. With this mixture stirred, 1.5 ml dichloroacetyl chloride was added dropwise to the mixture. The mixture was refluxed until a clear solution appeared. The mixture was stripped of solvent and subjected to Kugelrohr distillation (150° C. @ 0.25 mm Hg) to provide 2.7 g of product having the elemental analysis reported in Table I.

Workup

  1. temperatureThe mixture was refluxed until a clear solution
  2. distillationsubjected to Kugelrohr distillation (150° C. @ 0.25 mm Hg)

Sources & evidence

ORD record
ord-d15e90395e194ec0b8ded4610d4128fb
Source dataset
uspto-grants-1988_07
Patent number
US04755218

Reaction notes

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