Methyl Chloride → HCID 20133041, compound

HRID 844946Notes

Reaction equation

HRID 844946 reaction equation
[Cl:1][CH:2]([Cl:16])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]1[CH3:15])=[O:4].[CH3:17][CH2:18]CC(Cl)=O.C(C1C2C(=CC=CC=2)CCN1)CC.C1C2C(=CC=CC=2)C=CN=1.[OH-].[Na+].CCl.ClC(Cl)C(Cl)=O>O>[Cl:16][CH:2]([Cl:1])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]1[CH2:15][CH2:17][CH3:18])=[O:4]

Participants

9

Reactant 7

HCID 6327Methyl ChlorideHCID 6593Dichloroacetyl chlorideHCID 8405IsoquinolineHCID 8855Butyryl chlorideHCID 14798Sodium HydroxideHCID 11513839HCID 11513839, compoundHCID 179964412-(Dichloroacetyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 20133041HCID 20133041, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

By procedures described in Example 1, (Method A), phenethylamine and n-butyryl chloride were converted to 1-n-propyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 2.0 g of this isoquinoline compound, 10 ml 10% sodium hydroxide and 50 ml methyl 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 (150° C. @ 0.25 mm Hg) to provide 3.5 g of a viscous yellow oil 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 (150° C. @ 0.25 mm Hg)

Sources & evidence

ORD record
ord-e7eb4df6e8cd450fb9b96e2272e46cec
Source dataset
uspto-grants-1988_07
Patent number
US04755218

Reaction notes

Loading…