2-(2-aminoethylamino)ethanol

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:230.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 93.3 g of 2-(2-aminoethylamino)ethanol (0.9 moles) and 52.1 g of urea (0.87 moles) was heated slowly to 230° C. with stirring. The evolution of ammonia began when the temperature reached 130° C. The reaction mixture was heated at 230° C. for 2 hours. The mixture solidified to a light-yellow solid after it had cooled to room temperature to afford 110.5 g of hydroxyethylethyleneurea. Recrystallized from acetone, M.P.: 55-57.5° C.; 1H NMR (DMSO-d6): δ6.3 (s, 1H), 4.6 (s, 1H), 3.5-3.0 (m, 8H). reached 130° C The reaction mixture was heated at 230° C. for 2 hours had cooled to room temperature

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

Procedure: 2-(2-aminoethylamino)ethanol (10 g, 96.01 mmol) was added via syringe to a stirred solution of ethyl trifluoroacetate (13.64 g, 96.01 mmol) in dry Et2O (30 mL) at 0° C. The resulting solution was stirred at room temperature for 2 hours by which time a white precipitate had formed. The precipitate was removed by filtration, washed with Et2O (100 mL), and dried in vacuo for 3 hours to afford the title compound (13.6 g, 100%). 1H NMR (300 MHz, CDCl3) δ (t, J=5.1 Hz, 2H), 3.45 (t, J=5.6 Hz, 2H), 2.86 (t, J=5.6 Hz, 2H), 2.78 (t, J=4.9 Hz, 2H), 2.22 (br s, 2H); mass spectrum (API-TIS) m/z 201 (M+H). had formed The precipitate was removed by filtration washed with Et2O (100 mL) dried in vacuo for 3 hours

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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2 g of 4-fluoro-2-methyl-nitrobenzene, 1.61 g of 2-(2-aminoethylamino)ethanol and 2.14 g of K2CO3 were added to a solution of 20 ml of N-methylpyrrolidinone. The reaction medium was heated at 60° C. for 7 hours and, after cooling to room temperature, was then poured into a water and ice mixture. The yellow precipitate formed was filtered off, reslurried in water and then dried over P2O5. 1.3 g of 2-[2-(4-nitro-3-methylphenylamino)ethylamino]ethanol (7) were obtained. after cooling to room temperature The yellow precipitate formed was filtered off dried over P2O5

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2 g of 4-fluoro-2-methyl-nitrobenzene, 1.61 g of 2-(2-aminoethylamino)ethanol and 2.14 g of K2CO3 were added to a solution of 20 ml of N-methylpyrrolidinone. The reaction medium was heated at 60° C. for 7 hours and, after cooling to room temperature, was then poured into a water and ice mixture. The yellow precipitate formed was filtered off, reslurried in water and then dried over P2O5. 1.3 g of 2-[2-(4-nitro-3-methylphenylamino)ethylamino]ethanol (7) were obtained. after cooling to room temperature The yellow precipitate formed was filtered off dried over P2O5

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2 g of 4-fluoro-3-methyl nitrobenzene, 1.61 g of 2-(2-aminoethylamino)ethanol and 2.14 g of K2CO3 were added to a solution of 20 ml of N-methylpyrrolidinone. The reaction medium was heated at 60° C. for 7 hours and, after cooling to room temperature, was then poured into a water and ice mixture. The yellow precipitate formed was filtered off, reslurried in water and then dried over P2O5. 2.4 g of 2-[2-(4-nitro-2-methylphenylamino)ethylamino]ethanol (5) were obtained. after cooling to room temperature The yellow precipitate formed was filtered off dried over P2O5

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2 g of 4-fluoro-3-methyl nitrobenzene, 1.61 g of 2-(2-aminoethylamino)ethanol and 2.14 g of K2CO3 were added to a solution of 20 ml of N-methylpyrrolidinone. The reaction medium was heated at 60° C. for 7 hours and, after cooling to room temperature, was then poured into a water and ice mixture. The yellow precipitate formed was filtered off, reslurried in water and then dried over P2O5. 2.4 g of 2-[2-(4-nitro-2-methylphenylamino)ethylamino]ethanol (5) were obtained. after cooling to room temperature The yellow precipitate formed was filtered off dried over P2O5

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

Procedure: Employing the reaction equipment and general procedures described in Example I, a solution of 229.0 g. (3.75 moles) monoethanolamine and 225.0 g. (3.75 moles) ethylenediamine was admixed with 6.25 g. (0.054 mole; 2.3wt.% and 1.44 mole%, basis MEA) 85% phosphoric acid and heated at 250° C. under 225 - 225 psig pressure for 2.0 hours. Analysis of the reaction product by gas-liquid chromatography (GLC Area %) showed a total conversion of reactants of only 4.7% was obtained. The reaction products were 95.0 diethylenetriamine, 2.5 piperazine and 2.5 Area % N-(2-aminoethyl)-ethanolamine. No higher polyethylene polyamines, e.g., triethylenetetramine, tetraethylenepentamine, etc. were formed. was obtained