N-benzyl-4-phenylbutan-2-amine

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: A solution of 2-amino-5-(2-bromoacetyl)benzenesulphonamide (0.5 g), N-(1-methyl-3-phenylpropyl)-N-(phenylmethyl) amine (0.45 g) and propylene oxide (2.5 ml) in 2-butanone (30 ml) was heated under reflux for 3 hours. The solution was then concentrated to a red-brown oil (0.7 g) which was dissolved in absolute ethanol (30 ml) and treated with sodium borohydride (258 mg) at room temperature during 2 hours. Excess borohydride was then destroyed with 2N hydrochloric acid and the ethanol was removed under reduced pressure. The residue was basified with 8% sodium bicarbonate and extracted with ethyl acetate (3 × 50 ml). The extracts were washed with water (100 ml), dried and concentrated to an orange oil (0.63 g). The oil was dissolved in acetone (10 ml) and re-precipitated as an orange solid (340 mg) by addition of petroleum ether (b.p. 60°-80°). Chromatographic purification of this solid on silica plates [Merck St17; elution with chloroform: methanol (5:1 )] and conversion of the product into a hydrochloride salt gave the title compound, 0.2 g, m.p. 133°-136°. under reflux for 3 hours The solution was then concentrated to a red-brown oil (0.7 g) which was dissolved in absolute ethanol (30 ml) treated with sodium borohydride (258 mg) at room temperature during 2 hours Excess borohydride was then destroyed with 2N hydrochloric acid the ethanol was removed under reduced pressure extracted with ethyl acetate (3 × 50 ml) The extracts were washed with water (100 ml) dried concentrated to an orange oil (0.63 g) The oil was dissolved in acetone (10 ml) re-precipitated as an orange solid (340 mg) by addition of petroleum ether (b.p. 60°-80°) Chromatographic purification of this solid on silica plates [Merck St17; elution with chloroform: methanol (5:1 )] and conversion of the product into a hydrochloride salt

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

Procedure: A mixture of 5-(2-bromoacetyl)-2-chlorobenzenesulphonamide (3.13 g) in butanone (50 ml) and N-(1-methyl-3-phenylpropyl)-N-(phenylmethyl)amine (4.8 g) was heated under reflux for 30 minutes. The solvent was removed under reduced pressure and the residue triturated with dry ether and filtered. The ether solution was evaporated to dryness and the product dissolved in ethanol (50 ml) and treated with sodium borohydride (0.3 g). The mixture was stirred for 30 minutes and a further aliquot of sodium borohydride (0.3 g) was added. The reaction mixture was acidified with 2N hydrochloric acid and the ethanol removed under reduced pressure. The concentrate was bastified with 5N sodium hydroxide and the mixture extracted with ethyl acetate (2 × 50 ml). The extracts were washed with water (2 × 50 ml), dried (MgSO4) and evaporated to dryness to give the product as a yellow oil, 4.6 g. This oil was purified by chromatography on preparative chromatographic plates (silica, CHCl3 /5% MeOH) and converted into a hydrochloride salt m.p. 120-125°. was heated under reflux for 30 minutes The solvent was removed under reduced pressure the residue triturated with dry ether filtered The ether solution was evaporated to dryness the product dissolved in ethanol (50 ml) treated with sodium borohydride (0.3 g) a further aliquot of sodium borohydride (0.3 g) was added the ethanol removed under reduced pressure the mixture extracted with ethyl acetate (2 × 50 ml) The extracts were washed with water (2 × 50 ml) dried (MgSO4) evaporated to dryness