1-[2-(2-hydroxypropylamino)ethylamino]propan-2-ol

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

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Glycidyl methacrylate (4.8g, 34 mmol) and 4-methoxyphenol (0.13 g) were added to a solution of N,N'-bis-(2-hydroxypropyl)ethylenediamine (IV-a) (3.0 g, 17 mmol) in 80 mL of methanol at 0° C. The mixture was brought to room temperature and maintained for eight days, followed by heating for 24 hours at 30° C. A quantitative yield of a viscous, slightly brown liquid was obtained after removal of the solvent. The product was further purified by dissolving the liquid in water followed by the addition of sodium chloride to saturation. The oil layer was separated, dissol ved in CH2Cl2 and dried over magnesium sulfate. Filtration and removal of solvent yielded Quadrol dimethylacrylate (VII-a) [yield 48 percent: IR(neet):3350(broad OH); 1700 (C=O); 1620(C=C); NMR (CDCl3): δ6.1(s,2H); 5.6(s,2H); 3.8(broad m,8H); 2.6(broad m,12); 2.0(s,6H); 1.1(d,6H)]. was brought to room temperature maintained for eight days A quantitative yield of a viscous, slightly brown liquid was obtained after removal of the solvent The product was further purified by dissolving the liquid in water followed by the addition of sodium chloride to saturation The oil layer was separated dried over magnesium sulfate Filtration and removal of solvent

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Glycidyl methacrylate (4.8g, 34 mmol) and 4-methoxyphenol (0.13 g) were added to a solution of N,N'-bis-(2-hydroxypropyl)ethylenediamine (IV-a) (3.0 g, 17 mmol) in 80 mL of methanol at 0° C. The mixture was brought to room temperature and maintained for eight days, followed by heating for 24 hours at 30° C. A quantitative yield of a viscous, slightly brown liquid was obtained after removal of the solvent. The product was further purified by dissolving the liquid in water followed by the addition of sodium chloride to saturation. The oil layer was separated, dissol ved in CH2Cl2 and dried over magnesium sulfate. Filtration and removal of solvent yielded Quadrol dimethylacrylate (VII-a) [yield 48 percent: IR(neet):3350(broad OH); 1700 (C=O); 1620(C=C); NMR (CDCl3): δ6.1(s,2H); 5.6(s,2H); 3.8(broad m,8H); 2.6(broad m,12); 2.0(s,6H); 1.1(d,6H)]. was brought to room temperature maintained for eight days A quantitative yield of a viscous, slightly brown liquid was obtained after removal of the solvent The product was further purified by dissolving the liquid in water followed by the addition of sodium chloride to saturation The oil layer was separated dried over magnesium sulfate Filtration and removal of solvent

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

Procedure: (V-a): Propylene oxide (181.6 g, 0.3 mol) in 25 mL of absolute ethanol was added dropwise for 4.5 hours to a solution of N,N'-bis(2-hydroxypropyl)ethylenediamine (IV-a) (55 g, 0.3 mol) in 50 mL each of absolute ethanol, methanol and distilled water at 80° C. The reaction mixture was cooled and concentrated to give a milky white viscous suspension. The suspension was dissolved in ether and dried over anhydrous sodium sulfate. Unreacted (IV-a) precipitated and was removed by filtration. Ether was removed from the clear filtrate to produce a viscous liquid. Fractional distillation of the oil produced N,N,N'-tris(2-hydroxypropyl)ethylenediamine[bp. 140° C. at 0.15 mm; yield 55 percent; IR(neet); 3350(broad OH); NMR(CDCl3): δ 3.8(broad m,3H); 2.5(broad m,10H); 1.1(d,9H)]. distilled water at 80° C The reaction mixture was cooled concentrated to give a milky white viscous suspension dried over anhydrous sodium sulfate Unreacted (IV-a) precipitated was removed by filtration Ether was removed from the clear filtrate to produce a viscous liquid Fractional distillation of the oil

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (IV-a): Propylene oxide (142.4 g, 2.4 mol) was added dropwise over a period of 11 hours to a solution of ethylenediamine (71.9 g, 1.2 mol) in 25 mL absolute ethanol and 10 mL of nitrogen purged distilled water at 90° C. After addition, the reaction was maintained for an additional hour, then cooled to room temperature (about 20° C.). The reaction solution was concentrated by rotary evaporation to give a milky white suspension which, upon dissolution in anhydrous ether, produced a white precipitate of N,N'-bis(2-hydroxypropyl)ethylenediamine in 28.5 percent yield. The product was crystallized from methanol/ethanol [m.p. 132° C., IR(Nujol): 3250(OH); NMR(MeOHd4): δ3.8(m,2H); 2.6(t,8H); 1.2(d,6H)]. purged distilled water at 90° C After addition the reaction was maintained for an additional hour The reaction solution was concentrated by rotary evaporation to give a milky white suspension which

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

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

Procedure: (V-a): Propylene oxide (181.6 g, 0.3 mol) in 25 mL of absolute ethanol was added dropwise for 4.5 hours to a solution of N,N'-bis(2-hydroxypropyl)ethylenediamine (IV-a) (55 g, 0.3 mol) in 50 mL each of absolute ethanol, methanol and distilled water at 80° C. The reaction mixture was cooled and concentrated to give a milky white viscous suspension. The suspension was dissolved in ether and dried over anhydrous sodium sulfate. Unreacted (IV-a) precipitated and was removed by filtration. Ether was removed from the clear filtrate to produce a viscous liquid. Fractional distillation of the oil produced N,N,N'-tris(2-hydroxypropyl)ethylenediamine [bp. 140° C. at 0.15 mm; yield 55 percent; IR(neet): 3350(broad OH); NMR(CDCl3): δ 3.8(broad m, 3H); 2.5(broad m, 10H); 1.1(d, 9H)]. distilled water at 80° C The reaction mixture was cooled concentrated to give a milky white viscous suspension dried over anhydrous sodium sulfate Unreacted (IV-a) precipitated was removed by filtration Ether was removed from the clear filtrate to produce a viscous liquid Fractional distillation of the oil

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (IV-a): Propylene oxide (142.4 g, 2.4 mol) was added dropwise over a period of 11 hours to a solution of ethylenediamine (71.9 g, 1.2 mol) in 25 mL absolute ethanol and 10 mL of nitrogen purged distilled water at 90° C. After addition, the reaction was maintained for an additional hour, then cooled to room temperature (about 20° C.). The reaction solution was concentrated by rotary evaporation to give a milky white suspension which, upon dissolution in anhydrous ether, produced a white precipitate of N,N'-bis(2-hydroxypropyl)ethylenediamine in 28.5 percent yield. The product was crystallized from methanol/ethanol [m.p. 132° C., IR(Nujol):3250(OH); NMR(MeOHd4): δ3.8(m, 2H); 2.6(t, 8H); 1.2(d, 6H)]. purged distilled water at 90° C After addition the reaction was maintained for an additional hour The reaction solution was concentrated by rotary evaporation to give a milky white suspension which

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Glycidyl methacrylate (4.8g, 34 mmol) and 4-methoxyphenol (0.13 g) were added to a solution of N,N'-bis-(2-hydroxypropyl)ethylenediamine (IV-a) (3.0 g, 17 mmol) in 80 mL of methanol at 0° C. The mixture was brought to room temperature and maintained for eight days, followed by heating for 24 hours at 30° C. A quantitative yield of a viscous, slightly brown liquid was obtained after removal of the solvent. The product was further purified by dissolving the liquid in water followed by the addition of sodium chloride to saturation. The oil layer was separated, dissol ved in CH2Cl2 and dried over magnesium sulfate. Filtration and removal of solvent yielded Quadrol dimethylacrylate (VII-a) [yield 48 percent: IR(neet):3350(broad OH); 1700 (C=O); 1620(C=C); NMR (CDCl3): δ6.1(s,2H); 5.6(s,2H); 3.8(broad m,8H); 2.6(broad m,12); 2.0(s,6H); 1.1(d,6H)]. was brought to room temperature maintained for eight days A quantitative yield of a viscous, slightly brown liquid was obtained after removal of the solvent The product was further purified by dissolving the liquid in water followed by the addition of sodium chloride to saturation The oil layer was separated dried over magnesium sulfate Filtration and removal of solvent

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

Procedure: (V-a): Propylene oxide (181.6 g, 0.3 mol) in 25 mL of absolute ethanol was added dropwise for 4.5 hours to a solution of N,N'-bis(2-hydroxypropyl)ethylenediamine (IV-a) (55 g, 0.3 mol) in 50 mL each of absolute ethanol, methanol and distilled water at 80° C. The reaction mixture was cooled and concentrated to give a milky white viscous suspension. The suspension was dissolved in ether and dried over anhydrous sodium sulfate. Unreacted (IV-a) precipitated and was removed by filtration. Ether was removed from the clear filtrate to produce a viscous liquid. Fractional distillation of the oil produced N,N,N'-tris(2-hydroxypropyl)ethylenediamine[bp. 140° C. at 0.15 mm; yield 55 percent; IR(neet); 3350(broad OH); NMR(CDCl3): δ 3.8(broad m,3H); 2.5(broad m,10H); 1.1(d,9H)]. distilled water at 80° C The reaction mixture was cooled concentrated to give a milky white viscous suspension dried over anhydrous sodium sulfate Unreacted (IV-a) precipitated was removed by filtration Ether was removed from the clear filtrate to produce a viscous liquid Fractional distillation of the oil

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (IV-a): Propylene oxide (142.4 g, 2.4 mol) was added dropwise over a period of 11 hours to a solution of ethylenediamine (71.9 g, 1.2 mol) in 25 mL absolute ethanol and 10 mL of nitrogen purged distilled water at 90° C. After addition, the reaction was maintained for an additional hour, then cooled to room temperature (about 20° C.). The reaction solution was concentrated by rotary evaporation to give a milky white suspension which, upon dissolution in anhydrous ether, produced a white precipitate of N,N'-bis(2-hydroxypropyl)ethylenediamine in 28.5 percent yield. The product was crystallized from methanol/ethanol [m.p. 132° C., IR(Nujol): 3250(OH); NMR(MeOHd4): δ3.8(m,2H); 2.6(t,8H); 1.2(d,6H)]. purged distilled water at 90° C After addition the reaction was maintained for an additional hour The reaction solution was concentrated by rotary evaporation to give a milky white suspension which