2-(dimethylamino)-2-methylpropan-1-ol

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

Procedure: 22.4 g DP9C/012, 3.9 g Poly G 83-34, 1.0 g Pluronic L-62, 0.4 g trimethylolethane, 2.0 g Cirrasol G-265, 1.0 g DMAMP DBS, and 0.11 g tin catalyst are added to 2.6 g N-methyl pyrrolidone plus 4.7 g methylethylketone, 2.8 g tertiary amyl alcohol, 0.6 g 2,4-pentanedione and 4.0 g diacetone alcohol and are mixed together. The mixture is heated to 60° C. and then reacted for 6 hours in a nitrogen atmosphere. Following the reaction, the resulting polyurethane prepolymer mixture is cooled and then dispersed in 59.0 g of distilled water, 0.1 g trimethylolethane, and 0.2 g triethanolamine with a high shear disperser, resulting in a stable aqueous polyurethane dispersion having about 24% solids by weight of the dispersion. The resulting polyurethane comprises about 3% polyethylene oxide side chains by weight of the solids of the polyurethane, about 12% polyethylene oxide main chains by weight of the solids of the polyurethane, and about 48% blocked polyisocyanates by weight of the solids of the polyurethane. are mixed together reacted for 6 hours in a nitrogen atmosphere the reaction

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

Procedure: To toluene (100 ml), sodium hydroxide (16.7 g, 418 mmol) and 2-dimethylamino-2-methyl-1-propanol (23.4 g, 200 mmol) were added and the mixture was heated at reflux for 2 hours. After cooling to 70° C., β-dimethylaminoethyl chloride hydrochloride (28.8 g, 200 mmol) was added. Then, the mixture was heated at reflux for 5.5 hours. After cooling to room temperature, insolubles were separated by filtration and the organic phase was concentrated under reduced pressure. The residue was distilled under reduced pressure to obtain 10.3 g (in a yield of 27%) of the objective compound as a colorless liquid. the mixture was heated at reflux for 2 hours Then, the mixture was heated at reflux for 5.5 hours After cooling to room temperature insolubles were separated by filtration the organic phase was concentrated under reduced pressure The residue was distilled under reduced pressure

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

Procedure: 22.4 g DP9C/012, 3.9 g Poly G 83-34, 1.0 g Pluronic L-62, 0.4 g trimethylolethane, 2.0 g Cirrasol G-265, 1.0 g DMAMP DBS, and 0.11 g tin catalyst are added to 2.6 g N-methyl pyrrolidone plus 4.7 g methylethylketone, 2.8 g tertiary amyl alcohol, 0.6 g 2,4-pentanedione and 4.0 g diacetone alcohol and are mixed together. The mixture is heated to 60° C. and then reacted for 6 hours in a nitrogen atmosphere. Following the reaction, the resulting polyurethane prepolymer mixture is cooled and then dispersed in 59.0 g of distilled water, 0.1 g trimethylolethane, and 0.2 g triethanolamine with a high shear disperser, resulting in a stable aqueous polyurethane dispersion having about 24% solids by weight of the dispersion. The resulting polyurethane comprises about 3% polyethylene oxide side chains by weight of the solids of the polyurethane, about 12% polyethylene oxide main chains by weight of the solids of the polyurethane, and about 48% blocked polyisocyanates by weight of the solids of the polyurethane. are mixed together reacted for 6 hours in a nitrogen atmosphere the reaction

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

Procedure: 2-Dimethylamino-2-Methyl-1-Propyl Tributylstannyl Ether is prepared from 59.6 gm (0.1 mole) bis(tributyltin) oxide and 23.4 gm (0.2 mole) 2-dimethylamino-2-methyl-1-propanol in 200 ml benzene. This is stirred and heated to reflux in a system that contains a Dean-Starke tube. After 30 minutes water began to collect in the Dean-Starke tube and after 46 hours only 1.6 ml of water (theory 1.8 ml) had collected. Solvent is stripped off on a rotating evaporator to provide 78.3 gm of straw colored liquid. This is fractionated at reduced pressure to collect the desired product, 52.7 gm of water-white liquid (Percent yield - 65), at 132°-137° C. at 0.5 mm. Infrared spectral analysis shows this to be the desired ether. heated to reflux in a system that to collect in the Dean-Starke tube and after 46 hours only 1.6 ml of water (theory 1.8 ml) had collected Solvent is stripped off on a rotating evaporator to provide 78.3 gm of straw colored liquid to collect the desired product, 52.7 gm of water-white liquid (Percent yield - 65) at 132°-137° C.

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

Procedure: 2-Dimethylamino-2-Methyl-1-Propyl Tributylstannyl Ether is prepared from 59.6 gm (0.1 mole) bis(tributyltin) oxide and 23.4 gm (0.2 mole) 2-dimethylamino-2-methyl-1-propanol in 200 ml benzene. This is stirred and heated to reflux in a system that contains a Dean-Starke tube. After 30 minutes water began to collect in the Dean-Starke tube and after 46 hours only 1.6 ml of water (theory 1.8 ml) had collected. Solvent is stripped off on a rotating evaporator to provide 78.3 gm of straw colored liquid. This is fractionated at reduced pressure to collect the desired product, 52.7 gm of water-white liquid (Percent yield - 65), at 132°-137° C. at 0.5 mm. Infrared spectral analysis shows this to be the desired ether. heated to reflux in a system that to collect in the Dean-Starke tube and after 46 hours only 1.6 ml of water (theory 1.8 ml) had collected Solvent is stripped off on a rotating evaporator to provide 78.3 gm of straw colored liquid to collect the desired product, 52.7 gm of water-white liquid (Percent yield - 65) at 132°-137° C.

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

Procedure: DMAMP 118 g (1 mole) and commercial grade caprylic acid 131 g (1 mole) were dissolved in 35 ml of toluene. The mixture was heated under reflux at about 140°-165° until 20 ml distillate was recovered and no more was being collected. The pressure was then reduced to 10mm and distillation was continued to about 130° C to strip off toluene and water. The pressure was then reduced to about 1 mm and the main product fraction was recovered at a liquid temperature of about 106°-109°. There was obtained 2-dimethylamino-2-methyl-1-propyl caprylate, neutral equivalent 247.9 compared with theoretical 244. The mixture was heated under reflux at about 140°-165° until 20 ml distillate was recovered no more was being collected The pressure was then reduced to 10mm and distillation was continued to about 130° C the main product fraction was recovered at a liquid temperature of about 106°-109°

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

Procedure: DMAMP 118 g (1 mole) and commercial grade caprylic acid 131 g (1 mole) were dissolved in 35 ml of toluene. The mixture was heated under reflux at about 140°-165° until 20 ml distillate was recovered and no more was being collected. The pressure was then reduced to 10mm and distillation was continued to about 130° C to strip off toluene and water. The pressure was then reduced to about 1 mm and the main product fraction was recovered at a liquid temperature of about 106°-109°. There was obtained 2-dimethylamino-2-methyl-1-propyl caprylate, neutral equivalent 247.9 compared with theoretical 244. The mixture was heated under reflux at about 140°-165° until 20 ml distillate was recovered no more was being collected The pressure was then reduced to 10mm and distillation was continued to about 130° C the main product fraction was recovered at a liquid temperature of about 106°-109°

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

Procedure: To toluene (100 ml), sodium hydroxide (16.7 g, 418 mmol) and 2-dimethylamino-2-methyl-1-propanol (23.4 g, 200 mmol) were added and the mixture was heated at reflux for 2 hours. After cooling to 70° C., β-dimethylaminoethyl chloride hydrochloride (28.8 g, 200 mmol) was added. Then, the mixture was heated at reflux for 5.5 hours. After cooling to room temperature, insolubles were separated by filtration and the organic phase was concentrated under reduced pressure. The residue was distilled under reduced pressure to obtain 10.3 g (in a yield of 27%) of the objective compound as a colorless liquid. the mixture was heated at reflux for 2 hours Then, the mixture was heated at reflux for 5.5 hours After cooling to room temperature insolubles were separated by filtration the organic phase was concentrated under reduced pressure The residue was distilled under reduced pressure

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

Procedure: To toluene (100 ml), sodium hydroxide (16.7 g, 418 mmol) and 2-dimethylamino-2-methyl-1-propanol (23.4 g, 200 mmol) were added and the mixture was heated at reflux for 2 hours. After cooling to 70° C., β-dimethylaminoethyl chloride hydrochloride (28.8 g, 200 mmol) was added. Then, the mixture was heated at reflux for 5.5 hours. After cooling to room temperature, insolubles were separated by filtration and the organic phase was concentrated under reduced pressure. The residue was distilled under reduced pressure to obtain 10.3 g (in a yield of 27%) of the objective compound as a colorless liquid. the mixture was heated at reflux for 2 hours Then, the mixture was heated at reflux for 5.5 hours After cooling to room temperature insolubles were separated by filtration the organic phase was concentrated under reduced pressure The residue was distilled under reduced pressure

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

Procedure: To toluene (100 ml), sodium hydroxide (16.7 g, 418 mmol) and 2-dimethylamino-2-methyl-1-propanol (23.4 g, 200 mmol) were added and the mixture was heated at reflux for 2 hours. After cooling to 70° C., β-dimethylaminoethyl chloride hydrochloride (28.8 g, 200 mmol) was added. Then, the mixture was heated at reflux for 5.5 hours. After cooling to room temperature, insolubles were separated by filtration and the organic phase was concentrated under reduced pressure. The residue was distilled under reduced pressure to obtain 10.3 g (in a yield of 27%) of the objective compound as a colorless liquid. the mixture was heated at reflux for 2 hours Then, the mixture was heated at reflux for 5.5 hours After cooling to room temperature insolubles were separated by filtration the organic phase was concentrated under reduced pressure The residue was distilled under reduced pressure

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-chloro-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridine (from Example 4; 100 mg, 0.39 mmol), 2-(dimethylamino)-2-methyl-1-propanol (68 μl, 0.58 mmol) and 1.0 M potassium tert-butoxide in tert-butanol (0.8 mL, 0.80 mmol) in 4 mL of toluene was heated at 100° C. for 1 day. The organic phase was washed with 3×2 mL of water and 2 mL of brine. The organic phase was shaken at 50° C. with 4 mL of 2.0 M acetic acid for 2 days. The aqueous phase was washed with 3×3 mL of ethyl acetate, made basic by addition of potassium hydroxide, saturated with sodium chloride and extracted with 3×2 mL of ethyl acetate. The organic phase was dried (MgSO4) and concentrated under reduced pressure to give 79 mg (0.31 mmol, 80%) of the title compound as a colorless oil. LC-UV purity 95%. MS m/z 255 (M+1)+, calc. 255 (M+1)+. The organic phase was washed with 3×2 mL of water and 2 mL of brine The aqueous phase was washed with 3×3 mL of ethyl acetate made basic by addition of potassium hydroxide, saturated with sodium chloride extracted with 3×2 mL of ethyl acetate The organic phase was dried (MgSO4) concentrated under reduced pressure

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

Procedure: To toluene (100 ml), sodium hydroxide (16.7 g, 418 mmol) and 2-dimethylamino-2-methyl-1-propanol (23.4 g, 200 mmol) were added and the mixture was heated at reflux for 2 hours. After cooling to 70° C., β-dimethylaminoethyl chloride hydrochloride (28.8 g, 200 mmol) was added. Then, the mixture was heated at reflux for 5.5 hours. After cooling to room temperature, insolubles were separated by filtration and the organic phase was concentrated under reduced pressure. The residue was distilled under reduced pressure to obtain 10.3 g (in a yield of 27%) of the objective compound as a colorless liquid. the mixture was heated at reflux for 2 hours Then, the mixture was heated at reflux for 5.5 hours After cooling to room temperature insolubles were separated by filtration the organic phase was concentrated under reduced pressure The residue was distilled under reduced pressure