Phenethylamine → 2-(2-Chloropropionyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

HRID 844953

Reaction equation

HRID 844953 reaction equation
C(N)CC1C=CC=CC=1.C(Cl)(=O)C1C=CC=CC=1.[C:19]1([CH:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27][NH:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1C2C(=CC=CC=2)C=CN=1.[OH-].[Na+].[Cl:47][CH:48]([CH3:52])[C:49](Cl)=[O:50]>O.C(Cl)Cl>[Cl:47][CH:48]([CH3:52])[C:49]([N:26]1[CH2:27][CH2:28][C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:25]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:50]

Participants

9

Reactant 6

HCID 1001PhenethylamineHCID 7412Benzoyl chlorideHCID 8405IsoquinolineHCID 14798Sodium HydroxideHCID 1001371,2,3,4-Tetrahydro-1-phenylisoquinolineHCID 1110192-Chloropropionyl chloride

Product 1

HCID 201330512-(2-Chloropropionyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

By procedures described in Example 1 (Method A), phenethylamine and benzoyl chloride were converted to 1-phenyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 3.0 g of this isoquinoline compound, 5 ml 10% sodium hydroxide and 50 ml methylene chloride. With this mixture stirred, 1 ml 2-chloropropionyl chloride was added dropwise to the mixture. The mixture was stirred for 10 minutes, then water was added. The organic extract was dried with magnesium sulfate, stripped of solvent and subjected to Kugelrohr distillation (170° C. @ 0.1 mm Hg) to provide 2.3 g of a viscous yellow oil product having the elemental analysis reported in Table I.

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. extractionThe organic extract
  3. dry with materialwas dried with magnesium sulfate
  4. distillationsubjected to Kugelrohr distillation (170° C. @ 0.1 mm Hg)

Sources & evidence

ORD record
ord-8104b3380a254884baca8cfa441d0576
Source dataset
uspto-grants-1988_07
Patent number
US04755218

Linked notes

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