N'-ethylethane-1,2-diamine

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: Into a mixture comprising 8 g of a diethyl ester of oxalic acid and 8 ml of ethanol was dropped at room temperature 4.4 g of N-ethyl ethylenediamine. The resulting mixture was allowed to react for 3 hours, and then heated to remove the ethanol. Subsequently, the residue was recrystallized from 10 ml of dioxane to obtain 5.4 g of 1-ethyl-2,3-dioxo-piperazine, m.p. 124° C, yield 76.0%. to react for 3 hours heated to remove the ethanol Subsequently, the residue was recrystallized from 10 ml of dioxane

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

Procedure: 143 g of N-(cyanomethyl) 2-acetoxy 4-acetamino 5-chlorobenzamide was introduced into a one liter balloon flask provided with sealed agitator, a reflux condenser on which there was disposed a bubble counter containing vaseline oil, a thermometer and a dropping funnel. Thereafter, 123 g of N-ethyl ethylene diamine were rapidly added dropwise. The reaction was exothermic. The temperature rose to 110° C. and the amount of gas evolved was substantial. A thick solution was obtained. The solution was heated to temperature of 120° and then, after 25 minutes of heating, drops of carbon disulphide were added and the temperature was then maintained at 120° for a further period of 20 minutes until the gas ceased to be evolved. provided with sealed agitator, a reflux condenser on which there containing vaseline oil rose to 110° C. A thick solution was obtained The solution was heated to temperature of 120° after 25 minutes of heating the temperature was then maintained at 120° for a further period of 20 minutes until the gas

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

Procedure: 143 g of N-(cyanomethyl) 2-acetoxy 4-acetamino 5-chlorobenzamide was introduced into a one liter balloon flask provided with sealed agitator, a reflux condenser on which there was disposed a bubble counter containing vaseline oil, a thermometer and a dropping funnel. Thereafter, 123 g of N-ethyl ethylene diamine were rapidly added dropwise. The reaction was exothermic. The temperature rose to 110° C. and the amount of gas evolved was substantial. A thick solution was obtained. The solution was heated to temperature of 120° and then, after 25 minutes of heating, drops of carbon disulphide were added and the temperature was then maintained at 120° for a further period of 20 minutes until the gas ceased to be evolved. provided with sealed agitator, a reflux condenser on which there containing vaseline oil rose to 110° C. A thick solution was obtained The solution was heated to temperature of 120° after 25 minutes of heating the temperature was then maintained at 120° for a further period of 20 minutes until the gas

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 47 mg (0.74 mmol) of copper and 225 mg (2.27 mmol) of copper(I) chloride were added to a solution of 1.35 g (15.0 mmol) of 2-bromothiazole and 9.48 ml (90.0 mmol) of N-ethylethylenediamine in isopropanol (7.5 ml). The mixture was then heated to 70° C. for 1 h. After cooling to RT, the reaction solution was poured into water and extracted with EA. The organic phase was dried over MgSO4, filtered and evaporated under a vacuum. 200 mg (1.2 mmol, 8%) of N1-ethyl-N1-(thiazol-2-yl)ethane-1,2-diamine were obtained by carrying out CC twice (i. DCE/EtOH 5:1; ii. DCE/EtOH/conc. aq. NH4OH soln. 5:1:0.06) with the residue. After cooling to RT extracted with EA The organic phase was dried over MgSO4 filtered evaporated under a vacuum

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 47 mg (0.74 mmol) of copper and 225 mg (2.27 mmol) of copper(I) chloride were added to a solution of 1.35 g (15.0 mmol) of 2-bromothiazole and 9.48 ml (90.0 mmol) of N-ethylethylenediamine in isopropanol (7.5 ml). The mixture was then heated to 70° C. for 1 h. After cooling to RT, the reaction solution was poured into water and extracted with EA. The organic phase was dried over MgSO4, filtered and evaporated under a vacuum. 200 mg (1.2 mmol, 8%) of N1-ethyl-N1-(thiazol-2-yl)ethane-1,2-diamine were obtained by carrying out CC twice (i. DCE/EtOH 5:1; ii. DCE/EtOH/conc. aq. NH4OH soln. 5:1:0.06) with the residue. After cooling to RT extracted with EA The organic phase was dried over MgSO4 filtered evaporated under a vacuum

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

Procedure: The title compound is prepared by reacting 3-(phenylsulfonyl)piperidine with phosgene and reacting the resulting 3-(phenylsulfonyl)pyrrolidine with N-ethylethylenediamine.

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

Procedure: The title compound is prepared by reacting 3-(phenylsulfonyl)piperidine with phosgene and reacting the resulting 3-(phenylsulfonyl)piperidine-1-carbonylchloride with N-ethylethylenediamine.

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

Procedure: A fine powder of 5-nitro-2-indolecarboxylic acid ethyl ester (0.8 g, 3.41 mmol) was suspended in 2 ml of N-ethylethylenediamine under argon and the reaction mixture was stood at 55° C. overnight. The mixture was co-evaporated with toluene to dryness. The brown solid obtained was dissolved in 6 ml of ethyl acetate and 40 ml of ether was added to precipitate the product. After centrifugation, the liquid was poured out and the solid was washed with 30 ml of ether and dried to give small brown crystals (0.77 g, 82%). ESI MS: 277.11 (M+H+), 299.09 (M+Na+). 1H NMR (DMSO-d6) δ8.67 (d, 1H), 8.04 (dd, 1H), 7.55 (d, 1H), 7.37 (s), 3.36 (m, 3H), 2.69 (q, 2H), 2.55 (q, 2H), 0.99 (t, 3H). The brown solid obtained to precipitate the product After centrifugation, the liquid was poured out the solid was washed with 30 ml of ether dried

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

Procedure: A fine powder of 5-nitro-2-indolecarboxylic acid ethyl ester (0.8 g, 3.41 mmol) was suspended in 2 ml of N-ethylethylenediamine under argon and the reaction mixture was stood at 55° C. overnight. The mixture was co-evaporated with toluene to dryness. The brown solid obtained was dissolved in 6 ml of ethyl acetate and 40 ml of ether was added to precipitate the product. After centrifugation, the liquid was poured out and the solid was washed with 30 ml of ether and dried to give small brown crystals (0.77 g, 82%). ESI MS: 277.11 (M+H+), 299.09 (M+Na+). 1H NMR (DMSO-d6) δ8.67 (d, 1H), 8.04 (dd, 1H), 7.55 (d, 1H), 7.37 (s), 3.36 (m, 3H), 2.69 (q, 2H), 2.55 (q, 2H), 0.99 (t, 3H). The brown solid obtained to precipitate the product After centrifugation, the liquid was poured out the solid was washed with 30 ml of ether dried

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

Procedure: A mixture of 2-fluoro-4-nitrobenzonitrile (13.2 g), N-ethylethylenediamine (16 mL) and potassium carbonate (10 g) in acetonitrile (250 mL) was vigorously stirred for 16 hours resulting in the formation of an orange solid. The mixture was diluted with water and filtered. The precipitate was washed with water and dried to provide 2-(2-methylamino-ethylamino)-4-nitro-benzonitrile (10 g): 1H NMR (300 MHz, CDCl3) δ 7.65 (d, 1H), 7.55 (m, 2H), 5.8 (br, 1H), 3.4 (q, 2H), 3.1 (m, 2H), 2.8 (q, 2H), 1.2 (t, 3H). resulting in the formation of an orange solid filtered The precipitate was washed with water dried