4-methyl-1,2,3,4-tetrahydroisoquinoline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. The mixture was stirred for 15 minutes The organic extract was dried with magnesium sulfate subjected to Kugelrohr distillation (150° C. @ 0.1 mm Hg) to provide a product

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. The mixture was stirred for 15 minutes The organic extract was dried with magnesium sulfate subjected to Kugelrohr distillation (150° C. @ 0.1 mm Hg) to provide a product

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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 4-methyl-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, 2 ml dichloroacetyl chloride was added dropwise to the mixture. The mixture was stirred for 5 minutes, then water was added. The organic extract was dried with magnesium sulfate, stripped of solvent and subjected to Kugelrohr distillation (160° C. @ 0.1 mm Hg) to provide 4 g of a yellow oil product having the elemental analysis reported in Table I. The mixture was stirred for 5 minutes The organic extract was dried with magnesium sulfate subjected to Kugelrohr distillation (160° C. @ 0.1 mm Hg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By procedures described in Example 1 (Method A), β-methyl-phenethylamine and isobutyryl chloride were converted to -4-methyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 3.0 g of this isoquinoline compound, 10 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 and stripped of solvent. The residue was recrystallized from aqueous ethanol to provide 4 g of a white needle-crystalline product having the elemental analysis reported in Table I. The mixture was stirred for 2 minutes The organic extract was dried with magnesium sulfate The residue was recrystallized from aqueous ethanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared in analogy to example 1.1 from 4-methyl-1,2,3,4-tetrahydro-isoquinoline (CA [110841-71-9]) and 2-isopropoxy-5-methanesulfonyl-benzoic acid (Example 2.1).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. The mixture was stirred for 15 minutes The organic extract was dried with magnesium sulfate subjected to Kugelrohr distillation (150° C. @ 0.1 mm Hg) to provide a product

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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 4-methyl-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, 2 ml dichloroacetyl chloride was added dropwise to the mixture. The mixture was stirred for 5 minutes, then water was added. The organic extract was dried with magnesium sulfate, stripped of solvent and subjected to Kugelrohr distillation (160° C. @ 0.1 mm Hg) to provide 4 g of a yellow oil product having the elemental analysis reported in Table I. The mixture was stirred for 5 minutes The organic extract was dried with magnesium sulfate subjected to Kugelrohr distillation (160° C. @ 0.1 mm Hg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By procedures described in Example 1 (Method A), β-methyl-phenethylamine and isobutyryl chloride were converted to -4-methyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 3.0 g of this isoquinoline compound, 10 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 and stripped of solvent. The residue was recrystallized from aqueous ethanol to provide 4 g of a white needle-crystalline product having the elemental analysis reported in Table I. The mixture was stirred for 2 minutes The organic extract was dried with magnesium sulfate The residue was recrystallized from aqueous ethanol