2-(4-chlorophenyl)-N-methylethanamine

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

Procedure: 16.9 g (0.1 mol) of N-methyl-2-(4-chlorophenyl)ethylamine were dissolved in 30 ml of dimethylformamide and treated with 20.7 g (0.3 mol) of anhydrous potassium carbonate. The mixture was stirred at 5° and treated with 12.6 ml (0.11 mol) of 1-bromo-2-methyl-3-chloropropane, whereupon the mixture was stirred at 30° for a further 4 hours, the solvent was evaporated at 30° under reduced pressure and the residue was treated with water. The separated oil was extracted three times with ether. The organic extracts were dried over magnesium sulphate and evaporated under reduced pressure. The residual oil was distilled at 135°-140°/260 Pa, whereby there was obtained rac-4-chloro-N-(3-chloro-2-methylpropyl)-N-methylphenethylamine as a colourless oil which was used directly in the next step. MS: 260 (M)+. was stirred at 30° for a further 4 hours the solvent was evaporated at 30° under reduced pressure the residue was treated with water The separated oil was extracted three times with ether The organic extracts were dried over magnesium sulphate evaporated under reduced pressure The residual oil was distilled at 135°-140°/260 Pa

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

Procedure: A mixture containing 3-bromo-1-cyano-1,1-diphenylpropane (0.9 g-see Preparation 4), N-methyl-4-chlorophenethylamine (0.51 g, see CA 61:15224h), anhydrous potassium carbonate (0.83 g) and acetonitrile (40 ml) was heated under reflux for 24 hours then partitioned between dichloromethane (50 ml) and water (50 ml). The dichloromethane layer was dried (Na2SO4) and concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with hexane containing dichloromethane (25% up to 40%) and then with dichloromethane containing methanol (0% up to 5%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a gum, yield, 0.25 g. was heated under reflux for 24 hours then partitioned between dichloromethane (50 ml) and water (50 ml) The dichloromethane layer was dried (Na2SO4) concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with hexane containing dichloromethane (25% up to 40%) with dichloromethane containing methanol (0% up to 5%) concentrated in vacuo

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

Procedure: 16.9 g (0.1 mol) of N-methyl-2-(4-chlorophenyl)ethylamine were dissolved in 30 ml of dimethylformamide and treated with 20.7 g (0.3 mol) of anhydrous potassium carbonate. The mixture was stirred at 5° and treated with 12.6 ml (0.11 mol) of 1-bromo-2-methyl-3-chloropropane, whereupon the mixture was stirred at 30° for a further 4 hours, the solvent was evaporated at 30° under reduced pressure and the residue was treated with water. The separated oil was extracted three times with ether. The organic extracts were dried over magnesium sulphate and evaporated under reduced pressure. The residual oil was distilled at 135°-140°/260 Pa, whereby there was obtained rac-4-chloro-N-(3-chloro-2-methylpropyl)-N-methylphenethylamine as a colourless oil which was used directly in the next step. MS: 260 (M)+. was stirred at 30° for a further 4 hours the solvent was evaporated at 30° under reduced pressure the residue was treated with water The separated oil was extracted three times with ether The organic extracts were dried over magnesium sulphate evaporated under reduced pressure The residual oil was distilled at 135°-140°/260 Pa

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

Procedure: A mixture containing 3-bromo-1-cyano-1,1-diphenylpropane (0.9 g--see Preparation 4), N-methyl-4-chlorophenethylamine (0.51 g, see CA 61:15224h), anhydrous potassium carbonate (0.83 g) and acetonitrile (40 ml) was heated under reflux for 24 hours then partitioned between dichloromethane (50 ml) and water (50 ml). The dichloromethane layer was dried (Na2SO4) and concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with hexane containing dichloromethane (25% up to 40%) and then with dichloromethane containing methanol (0% up to 5%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a gum yield, 0.25 g. was heated under reflux for 24 hours then partitioned between dichloromethane (50 ml) and water (50 ml) The dichloromethane layer was dried (Na2SO4) concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with hexane containing dichloromethane (25% up to 40%) with dichloromethane containing methanol (0% up to 5%) concentrated in vacuo