2-[(2-amino-2-methylpropyl)amino]ethanol

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 244.2 g (2.05 mol) of chloroform are added to 180 g (1.36 mol) of 2-(2-amino-2-methyl-propylamino)ethanol in 1204 ml of acetone. The mixture is cooled to 5° C. under stirring and a solution of 327 g (8.18 mol) of sodium hydroxide in 327 ml of water is slowly added, the temperature of the mixture being maintained at 0°–5° C. during the addition. The mixture is then stirred at this temperature for further 2 hours and at room temperature for 15 hours. Subsequently, the pH of the aqueous solution is corrected to 11 and the mixture is stirred for further 4 hours. Then, the mixture is filtered and the residue is washed with acetone. The filtrate and the acetone of washing are collected and evaporated under vacuum (70° C./24 mbar). The residue is distilled giving a white oil with a boiling point of 115° C. at 2.66 mbar. After cooling a solid product with a melting point of 91°–93° C. is obtained. the temperature of the mixture being maintained at 0°–5° C. during the addition The mixture is then stirred at this temperature for further 2 hours and at room temperature for 15 hours the mixture is stirred for further 4 hours Then, the mixture is filtered the residue is washed with acetone The filtrate and the acetone of washing are collected evaporated under vacuum (70° C./24 mbar) The residue is distilled giving a white oil with a boiling point of 115° C. at 2.66 mbar After cooling a solid product with a melting point of 91°–93° C. is obtained

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 244.2 g (2.05 mol) of chloroform are added to 180 g (1.36 mol) of 2-(2-amino-2-methyl-propylamino)ethanol in 1204 ml of acetone. The mixture is cooled to 5° C. under stirring and a solution of 327 g (8.18 mol) of sodium hydroxide in 327 ml of water is slowly added, the temperature of the mixture being maintained at 0°–5° C. during the addition. The mixture is then stirred at this temperature for further 2 hours and at room temperature for 15 hours. Subsequently, the pH of the aqueous solution is corrected to 11 and the mixture is stirred for further 4 hours. Then, the mixture is filtered and the residue is washed with acetone. The filtrate and the acetone of washing are collected and evaporated under vacuum (70° C./24 mbar). The residue is distilled giving a white oil with a boiling point of 115° C. at 2.66 mbar. After cooling a solid product with a melting point of 91°–93° C. is obtained. the temperature of the mixture being maintained at 0°–5° C. during the addition The mixture is then stirred at this temperature for further 2 hours and at room temperature for 15 hours the mixture is stirred for further 4 hours Then, the mixture is filtered the residue is washed with acetone The filtrate and the acetone of washing are collected evaporated under vacuum (70° C./24 mbar) The residue is distilled giving a white oil with a boiling point of 115° C. at 2.66 mbar After cooling a solid product with a melting point of 91°–93° C. is obtained

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

Procedure: Neutralization with 2-amino-2-methyl-1-propanol or 2-amino-2-methyl-1-3-propandiol or triethanolamine is preferred.

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

Procedure: A mixture of urea (5.4 g, 91 mmol) and 2-((2-amino-2-methylpropyl)amino)ethanol (12 g, 91 mmol) was heated in a 200° C. sand bath for approximately 45 min until ammonia evolution had ceased. The crude mixture was purified by column chromatography, eluting from silica gel with a gradient of 0-10% methanol in dichloromethane to give 6.0 g of a white solid. 1H NMR (CDCl3, 400 MHz) δ 1.33 (s, 6H), 3.21 (s, 2H), 3.27-3.30 (t, J=5.2, 2H), 3.69-3.71 (q, J=5.2 Hz, 2H), 4.01-4.04 (t, J=5.4, 1H), 5.31 (br s, 1H); LRMS (ESI/APCI) m/z 159 [M+H]+. The crude mixture was purified by column chromatography eluting from silica gel with a gradient of 0-10% methanol in dichloromethane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-((2-amino-2-methylpropyl)amino)ethanol (12 g, 91 mmol) in 90 mL of acetone was added chloroform (10.9 mL, 136 mmol) and the solution was cooled to 0° C. with an external ice bath. A solution of NaOH (50% by weight, 43.6 g, 545 mmol) was added slowly to the cold solution over several minutes and the resultant solution was stirred at 0° C. for 2 hours then allowed to warm to room temperature and stirred for an additional 18 hr. The crude reaction mixture was filtered to remove solids, washing with acetone, and the solution was concentrated to 20 g of a clear oil. A portion of the crude material was purified by a bulb-to-bulb distillation under reduced pressure to give 1.45 g of a clear oil, which was used directly in the next step without further purification. LRMS (ESI/APCI) m/z 201 [M+H]+. to warm to room temperature The crude reaction mixture was filtered to remove solids washing with acetone the solution was concentrated to 20 g of a clear oil A portion of the crude material was purified by a bulb-to-bulb distillation under reduced pressure

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

Procedure: To a solution of 2-((2-methyl-2-nitropropyl)amino)ethanol (20.4 g, 126 mmol) in methanol (120 ml) was added a slurry of 50% Raney Nickel® in H2O (6 ml). The vessel was pressurized with H2 (450 psi) and the suspension stirred for 19 h. The mixture was filtered through Celite and concentrated in vacuo to give 20 g of a crude liquid, which was distilled under vacuum (<1 mbar, 100-125° C.) to give 13 g of a clear liquid, which was found to be partially purified and was used directly in the next step without purification. LRMS (ESI/APCI) m/z 133 [M+H]+. The mixture was filtered through Celite concentrated in vacuo to give 20 g of a crude liquid, which was distilled under vacuum (<1 mbar, 100-125° C.)

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

Procedure: A mixture of urea (5.4 g, 91 mmol) and 2-((2-amino-2-methylpropyl)amino)ethanol (12 g, 91 mmol) was heated in a 200° C. sand bath for approximately 45 min until ammonia evolution had ceased. The crude mixture was purified by column chromatography, eluting from silica gel with a gradient of 0-10% methanol in dichloromethane to give 6.0 g of a white solid. 1H NMR (CDCl3, 400 MHz) δ 1.33 (s, 6H), 3.21 (s, 2H), 3.27-3.30 (t, J=5.2, 2H), 3.69-3.71 (q, J=5.2 Hz, 2H), 4.01-4.04 (t, J=5.4, 1H), 5.31 (br s, 1H); LRMS (ESI/APCI) m/z 159 [M+H]+. The crude mixture was purified by column chromatography eluting from silica gel with a gradient of 0-10% methanol in dichloromethane

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

Procedure: To a solution of 2-((2-methyl-2-nitropropyl)amino)ethanol (9.7 g, 60 mmol) in Methanol (65 ml) was added a slurry of 50% Raney Nickel® in H2O (3 ml). The vessel was pressurized with H2 (450 psi) and the suspension stirred for 48 h. The mixture was filtered through Celite® and concentrated in vacuo to give 7.4 g of a crude liquid, which was used directly in the next step without purification. LRMS (ESI/APCI) m/z 133 [M+H]+. The mixture was filtered through Celite® concentrated in vacuo

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 244.2 g (2.05 mol) of chloroform are added to 180 g (1.36 mol) of 2-(2-amino-2-methylpropylamino)ethanol in 1204 ml of acetone. The mixture is cooled to 5° C. under stirring and a solution of 327 g (8.18 mol) of sodium hydroxide in 327 ml of water is slowly added, the temperature of the mixture being maintained at 0°-5° C. during the addition. The mixture is then stirred at this temperature for further 2 hours and at room temperature for 15 hours. Subsequently, the pH of the aqueous solution is corrected to 11 and the mixture is stirred for further 4 hours. Then, the mixture is filtered and the residue is washed with acetone. The filtrate and the acetone of washing are collected and evaporated under vacuum (70° C./24 mbar). The residue is distilled giving a white oil with a boiling point of 115° C. at 2.66 mbar. After cooling a solid product with a melting point of 91°-93° C. is obtained. the temperature of the mixture being maintained at 0°-5° C. during the addition The mixture is then stirred at this temperature for further 2 hours and at room temperature for 15 hours the mixture is stirred for further 4 hours Then, the mixture is filtered the residue is washed with acetone The filtrate and the acetone of washing are collected evaporated under vacuum (70° C./24 mbar) The residue is distilled giving a white oil with a boiling point of 115° C. at 2.66 mbar After cooling a solid product with a melting point of 91°-93° C. is obtained