N-decyldecan-1-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:

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 di-n-decylamine (10.9 g, 36.6 mmol) and 2-butene-1,4-diol diacetate (3.15 g, 18.3 mmol) in tetrahydrofuran (THF) (150 ml) is treated with tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.9 mmol) and stirred at room temperature overnight. The reaction mixture is concentrated in vacuo to a oil that is redissolved in THF (500 ml) and treated with 20% aqueous sodium hydroxide (250 ml). The mixture is stirred for one hour, concentrated, and extracted with ether. The ether extracts are dried and concentrated giving an orange oil which is purified by medium pressure chromatography (silica gel; 25% ethyl acetate in hexanes). The title compound is isolated as 5.8 g (49% yield) of a clear oil. The reaction mixture is concentrated in vacuo to a oil that is redissolved in THF (500 ml) treated with 20% aqueous sodium hydroxide (250 ml) The mixture is stirred for one hour concentrated extracted with ether The ether extracts are dried concentrated giving an orange oil which is purified by medium pressure chromatography (silica gel; 25% ethyl acetate in hexanes)

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

Procedure: A solution of di-n-decylamine (10.9 g, 36.6 mmol) and 2-butene-1,4-diol diacetate (3.15 g, 18.3 mmol) in tetrahydrofuran (THF) (150 ml) is treated with tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.9 mmol) and stirred at room temperature overnight. The reaction mixture is concentrated in vacuo to a oil that is redissolved in THF (500 ml) and treated with 20% aqueous sodium hydroxide (250 ml). The mixture is stirred for one hour, concentrated, and extracted with ether. The ether extracts are dried and concentrated giving an orange oil which is purified by medium pressure chromatography (silica gel; 25% ethyl acetate in hexanes). The title compound is isolated as 5.8 g (49% yield) of a clear oil. The reaction mixture is concentrated in vacuo to a oil that is redissolved in THF (500 ml) treated with 20% aqueous sodium hydroxide (250 ml) The mixture is stirred for one hour concentrated extracted with ether The ether extracts are dried concentrated giving an orange oil which is purified by medium pressure chromatography (silica gel; 25% ethyl acetate in hexanes)

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

Procedure: To a solution of 1.7 g (5.72 mmol) of didecylamine in 20 mL of CHCl3 was added 0.63 g (1.43 mmol) of 22. The reaction mixture was stirred at room temperature for 2 h under argon and concentrated under diminished pressure to give 3,7-bis(didecylamino)phenothiazin-5-ium bromide (CPD-14): mass spectrum (MALDI-TOF), m/z 788.69 (M+). concentrated under diminished pressure

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

Procedure: To a solution of 1.7 g (5.72 mmol) of didecylamine in 20 mL of CHCl3 was added 0.63 g (1.43 mmol) of 22. The reaction mixture was stirred at room temperature for 2 h under argon and concentrated under diminished pressure to give 3,7-bis(didecylamino)phenothiazin-5-ium bromide (CPD-14): mass spectrum (MALDI-TOF), m/z 788.69 (M+). concentrated under diminished pressure

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

Procedure: To 6.20 ml of an ice-cooled 20% solution of phosgene in toluene was slowly added a solution of 3 g 4-hydroxy-undecanoic acid hex-3-enyl ester and 0.93 g pyridine in 3 ml toluene. The reaction mixture was stirred for 16 hours at room temperature. A mixture of 3.48 g didecylamine and 0.93 g pyridine was added and the mixture was stirred for another 16 hours. Water was added and the mixture extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, 2N hydrochloric acid, water, dried over magnesium sulfate and evaporated to dryness. The residue was chromatographed on silica gel to give 2.9 g of a colorless liquid. was added the mixture was stirred for another 16 hours the mixture extracted with ethyl acetate The organic layer was washed with saturated sodium bicarbonate, 2N hydrochloric acid, water dried over magnesium sulfate evaporated to dryness The residue was chromatographed on silica gel

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

Procedure: To a solution of 1.7 g (5.72 mmol) of didecylamine in 20 mL of CHCl3 was added 0.63 g (1.43 mmol) of 22. The reaction mixture was stirred at room temperature for 2 h under argon and concentrated under diminished pressure to give 3,7-bis(didecylamino)phenothiazin-5-ium bromide (CPD-14): mass spectrum (MALDI-TOF), m/z 788.69 (M+). concentrated under diminished pressure

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

Procedure: A solution of di-n-decylamine (10.9 g, 36.6 mmol) and 2-butene-1,4-diol diacetate (3.15 g, 18.3 mmol) in tetrahydrofuran (THF) (150 ml) is treated with tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.9 mmol) and stirred at room temperature overnight. The reaction mixture is concentrated in vacuo to a oil that is redissolved in THF (500 ml) and treated with 20% aqueous sodium hydroxide (250 ml). The mixture is stirred for one hour, concentrated, and extracted with ether. The ether extracts are dried and concentrated giving an orange oil which is purified by medium pressure chromatography (silica gel; 25% ethyl acetate in hexanes). The title compound is isolated as 5.8 g (49% yield) of a clear oil. The reaction mixture is concentrated in vacuo to a oil that is redissolved in THF (500 ml) treated with 20% aqueous sodium hydroxide (250 ml) The mixture is stirred for one hour concentrated extracted with ether The ether extracts are dried concentrated giving an orange oil which is purified by medium pressure chromatography (silica gel; 25% ethyl acetate in hexanes)

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

Procedure: A solution of di-n-decylamine (10.9 g, 36.6 mmol) and 2-butene-1,4-diol diacetate (3.15 g, 18.3 mmol) in tetrahydrofuran (THF) (150 ml) is treated with tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.9 mmol) and stirred at room temperature overnight. The reaction mixture is concentrated in vacuo to a oil that is redissolved in THF (500 ml) and treated with 20% aqueous sodium hydroxide (250 ml). The mixture is stirred for one hour, concentrated, and extracted with ether. The ether extracts are dried and concentrated giving an orange oil which is purified by medium pressure chromatography (silica gel; 25% ethyl acetate in hexanes). The title compound is isolated as 5.8 g (49% yield) of a clear oil. The reaction mixture is concentrated in vacuo to a oil that is redissolved in THF (500 ml) treated with 20% aqueous sodium hydroxide (250 ml) The mixture is stirred for one hour concentrated extracted with ether The ether extracts are dried concentrated giving an orange oil which is purified by medium pressure chromatography (silica gel; 25% ethyl acetate in hexanes)