4-benzylaniline

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

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: 11.2 ml of bromine were added dropWise to a solution of 39.7 g of 4-benzylaniline and 33 g of ammonium thiocyanate in 400 ml of acetic acid at a temperature of from 12 to 18° C. After completion of the addition, the mixture was stirred at room temperature for 2 hours and then the solvent was distilled off. The residue was mixed with 600 ml of ethyl acetate and 300 ml of water and the mixture was neutralized by the addition of potassium carbonate powder The ethyl acetate layer was separated, washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residual solid was recrystallized from ethyl acetate to give 37.6 g of the title compound melting at 173-175° C. After completion of the addition the solvent was distilled off The residue was mixed with 600 ml of ethyl acetate and 300 ml of water the mixture was neutralized by the addition of potassium carbonate powder The ethyl acetate layer was separated washed with an aqueous solution of sodium chloride dried over anhydrous magnesium sulfate concentrated by evaporation under reduced pressure The residual solid was recrystallized from ethyl acetate

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of Ethyl-4,6-dichloroquinoline-3-carboxylate (1.0 g, 3.7 mmol) in 1,4-dioxane (10 mL) was added a solution of 4-benzylbenzenamine (733 mg, 4.0 mmol) in 1,4-dioxane (10 mL) at room temperature. After stirred at 85° C. 1 hour, the reaction mixture was then cooled down to room temperature and then treated with 20 mL of water. The resulting suspension treated with 10 NNaOH solutions to reach the pH about 9. It was partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography using a 9:1 v/v hexane:ethyl acetate as solvent to afford title compound (1.1 g, 65% yield) as a yellow solid. 1 hour, the reaction mixture was then cooled down to room temperature It was partitioned between ethyl acetate and water The organic layer was separated the aqueous layer was extracted with ethyl acetate The combined organic extracts were washed with brine dried over MgSO4 filtered concentrated The crude product was purified by flash column chromatography

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: The commercially available 4-benzyl aniline can be selectively brominated at the ortho position using n-bromosuccinimide in dimethylformamide to give the desired 2-bromo-4-benzyl aniline.

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

Procedure: 81 g of 4-benzylaniline, 1.2 g of aluminium powder, 3.6 g of anhydrous aluminium chloride and 100 g of but-1-ene are heated for 24 hours at +260° C. in an autoclave. After cooling, the reaction mass is poured into ice-cold dilute sodium hydroxide solution and taken up in ether. The ether phase is separated off, dried over sodium sulfate and subjected to fractional distillation; b.p. 130°-134° C./0.03 torr. Chromatographic purification on silica gel using hexane/ethyl acetate as eluant affords the title compound of formula ##STR12## in the form of a colourless oil; refractive index nD24 : 1.5579. After cooling the reaction mass is poured into ice-cold dilute sodium hydroxide solution The ether phase is separated off dried over sodium sulfate subjected to fractional distillation Chromatographic purification on silica gel

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

Procedure: 81 g of 4-benzylaniline, 1.2 g of aluminium powder, 3.6 g of anhydrous aluminium chloride and 100 g of but-1-ene are heated for 24 hours at +260° C. in an autoclave. After cooling, the reaction mass is poured into ice-cold dilute sodium hydroxide solution and taken up in ether. The ether phase is separated off, dried over sodium sulfate and subjected to fractional distillation; b.p. 130°-134° C./0.03 torr. Chromatographic purification on silica gel using hexane/ethyl acetate as eluant affords the title compound of formula ##STR12## in the form of a colourless oil; refractive index nD24 : 1.5579. After cooling the reaction mass is poured into ice-cold dilute sodium hydroxide solution The ether phase is separated off dried over sodium sulfate subjected to fractional distillation Chromatographic purification on silica gel

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolved 0.500 g 2-cyano-3,3-bis(methylthio)acrylamide in 15 mL EtOH and added 4-Aminodiphenylmethane (1.0 eq.). Stirred reaction at 75° C. until starting amide was absent by HPLC. Once complete (18 hrs), reaction was brought to room temperature and filtered to obtain a light yellow powder as product. Product was allowed to dry under vacuum for 1 hr. Product was then suspended in 10 mL EtOH and hydrazine hydrate (1 eq.) was added dropwise. Reaction was heated at 75° C. until intermediate was absent (HPLC). Once intermediate was absent (18 hrs), reaction was brought to room temperature and filtered to obtain a yellow powder as product. Product was allowed to dry under vacuum for 1 hr. reaction at 75° C. Once complete (18 hrs), reaction was brought to room temperature filtered to obtain a light yellow powder as product to dry under vacuum for 1 hr Reaction (18 hrs), reaction was brought to room temperature filtered to obtain a yellow powder as product to dry under vacuum for 1 hr

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolved 0.500 g 2-cyano-3,3-bis(methylthio)acrylamide in 15 mL EtOH and added 4-Aminodiphenylmethane (1.0 eq.). Stirred reaction at 75° C. until starting amide was absent by HPLC. Once complete (18 hrs), reaction was brought to room temperature and filtered to obtain a light yellow powder as product. Product was allowed to dry under vacuum for 1 hr. Product was then suspended in 10 mL EtOH and hydrazine hydrate (1 eq.) was added dropwise. Reaction was heated at 75° C. until intermediate was absent (HPLC). Once intermediate was absent (18 hrs), reaction was brought to room temperature and filtered to obtain a yellow powder as product. Product was allowed to dry under vacuum for 1 hr. reaction at 75° C. Once complete (18 hrs), reaction was brought to room temperature filtered to obtain a light yellow powder as product to dry under vacuum for 1 hr Reaction (18 hrs), reaction was brought to room temperature filtered to obtain a yellow powder as product to dry under vacuum for 1 hr