Benzoyl chloride → HCID 20133049, compound

HRID 844955Notes

Reaction equation

HRID 844955 reaction equation
[CH3:1][CH:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][NH2:4].[C:11](Cl)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC1C2C(=CC=CC=2)CNC1.C1C2C(=CC=CC=2)C=CN=1.[OH-].[Na+].[Cl:43][CH:44]([CH3:48])[C:45](Cl)=[O:46]>O.C(Cl)Cl>[Cl:43][CH:44]([CH3:48])[C:45]([N:4]1[CH2:3][CH:2]([CH3:1])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:46]

Participants

9

Reactant 6

HCID 7412Benzoyl chlorideHCID 8405IsoquinolineHCID 113982-PhenylpropylamineHCID 14798Sodium HydroxideHCID 1110192-Chloropropionyl chlorideHCID 137389344-Methyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 20133049HCID 20133049, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

By procedures described in Example 1 (Method A), β-methyl-phenethylamine and benzoyl chloride were converted to 4-methyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 4.0 g of this isoquinoline compound, 10 ml 10% sodium hydroxide and 50 ml methylene chloride. With this mixture stirred, 2 ml 2-chloropropionyl 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 subjected to Kugelrohr distillation (150° C. @ 0.1 mm Hg) to provide a product having the elemental analysis reported in Table I.

Workup

  1. stirringThe mixture was stirred for 15 minutes
  2. extractionThe organic extract
  3. dry with materialwas dried with magnesium sulfate
  4. distillationsubjected to Kugelrohr distillation (150° C. @ 0.1 mm Hg)
  5. customto provide a product

Sources & evidence

ORD record
ord-616c0c6a40004da1b5cd33478a9fbaed
Source dataset
uspto-grants-1988_07
Patent number
US04755218

Reaction notes

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