pentadecan-1-ol

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

Procedure: 1-tridecanol; 1-tetradecanol; 1-pentadecanol; 1-hexadecanol;

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

Procedure: Pentadecyl acrylate was prepared by esterification of acrylic acid with 1-pentadecanol under standard conditions. Crude monomer was recrystallized from three volumes of ethanol and dried in vacuo. Ten grams of pentadecyl acrylate was dissolved in 20 ml of oxygen free ethylacetate containing 0.10 grams of azobis-isobutylnitrile (hereinafter AIBN) and stirred in a sealed bottle maintained at 60° C. for 24 hours. The resulting polymer was isolated by precipitation into cold ethanol and dried in vacuo. Analysis of the polymer showed it to have a first order transition temperature of 29° C., a heat of fusion of 59 J/g and a molecular weight of about 175,000 in an uncured state. Crude monomer was recrystallized from three volumes of ethanol dried in vacuo Ten grams of pentadecyl acrylate was dissolved in 20 ml of oxygen free ethylacetate containing 0.10 grams of azobis-isobutylnitrile (hereinafter AIBN) and The resulting polymer was isolated by precipitation into cold ethanol dried in vacuo a first order transition temperature of 29° C. a heat of fusion of 59 J/g

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

Procedure: 1-tridecanol; 1-tetradecanol; 1-pentadecanol; 1-hexadecanol;

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

Procedure: A 250 mL three neck round bottom flask was equipped with an overhead stirrer, thermocouple, temperature controller and nitrogen sweep then charged with 10.0 g (25.34 mmol) of bendamustine hydrochloride, 5.85 g (25.6 mmol, 1.01 eq) of pentadecanol, 5.3 g (25.6 mmol, 1.01 eq) of dicyclohexylcarbodiimide (DCC), 100 mL of MDC and 0.31 g (2.54 mmol, 0.1 eq) of DMAP. The reaction was stirred at room temperature overnight at which time an in process analysis indicated the reaction was complete. Solids were removed by vacuum filtration and washed with 25 mL of MDC. The filtrate was washed with saturated aqueous sodium bicarbonate solution (2×100 mL), DI water (1×100 mL) and brine (1×100 mL) before drying over sodium sulfate, filtering and concentrating to dryness in vacuo to an off-white solid. This solid was triturated with 25 mL of MDC and the solid impurities were removed by vacuum filtration and washed with 5 mL of MDC. The filtrate was concentrated to dryness in vacuo to yield 10.8 g (19.0 mmol, 75%) of the product as an off-white solid with an HPLC purity of 94.6 A %. 1H NMR (400 MHz, CDCl3) δ 7.17 (d, J=8.76 Hz, 1H), 7.08 (d, J=2.32 Hz, 1H), 6.78 (dd, J=2.4, 8.76 Hz, 1H), 4.05 (t, J=6.8 Hz, 2 H), 3.72 (m, 4H), 3.69 (s, 3H), 3.63 (m, 4H), 2.91 (t, J=7.4 Hz, 2H), 2.49 (t, J=7.08 Hz, 2H), 2.18 (m, 2H), 1.60 (m, 2H), 1.32 (m, 24H), 0.88 (t, J=6.68 Hz, 3H). Solids were removed by vacuum filtration washed with 25 mL of MDC The filtrate was washed with saturated aqueous sodium bicarbonate solution (2×100 mL), DI water (1×100 mL) and brine (1×100 mL) before drying over sodium sulfate filtering concentrating to dryness in vacuo to an off-white solid This solid was triturated with 25 mL of MDC the solid impurities were removed by vacuum filtration washed with 5 mL of MDC The filtrate was concentrated to dryness in vacuo

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

Procedure: A 250 mL three neck round bottom flask was equipped with an overhead stirrer, thermocouple, temperature controller and nitrogen sweep then charged with 10.0 g (25.34 mmol) of bendamustine hydrochloride, 5.85 g (25.6 mmol, 1.01 eq) of pentadecanol, 5.3 g (25.6 mmol, 1.01 eq) of dicyclohexylcarbodiimide (DCC), 100 mL of MDC and 0.31 g (2.54 mmol, 0.1 eq) of DMAP. The reaction was stirred at room temperature overnight at which time an in process analysis indicated the reaction was complete. Solids were removed by vacuum filtration and washed with 25 mL of MDC. The filtrate was washed with saturated aqueous sodium bicarbonate solution (2×100 mL), DI water (1×100 mL) and brine (1×100 mL) before drying over sodium sulfate, filtering and concentrating to dryness in vacuo to an off-white solid. This solid was triturated with 25 mL of MDC and the solid impurities were removed by vacuum filtration and washed with 5 mL of MDC. The filtrate was concentrated to dryness in vacuo to yield 10.8 g (19.0 mmol, 75%) of the product as an off-white solid with an HPLC purity of 94.6A %. 1H NMR (400 MHz, CDCl3) δ 7.17 (d, J=8.76 Hz, 1H), 7.08 (d, J=2.32 Hz, 1H), 6.78 (dd, J=2.4, 8.76 Hz, 1H), 4.05 (t, J=6.8 Hz, 2H), 3.72 (m, 4H), 3.69 (s, 3H), 3.63 (m, 4H), 2.91 (t, J=7.4 Hz, 2H), 2.49 (t, J=7.08 Hz, 2H), 2.18 (m, 2H), 1.60 (m, 2H), 1.32 (m, 24H), 0.88 (t, J=6.68 Hz, 3H). Solids were removed by vacuum filtration washed with 25 mL of MDC The filtrate was washed with saturated aqueous sodium bicarbonate solution (2×100 mL), DI water (1×100 mL) and brine (1×100 mL) before drying over sodium sulfate filtering concentrating to dryness in vacuo to an off-white solid This solid was triturated with 25 mL of MDC the solid impurities were removed by vacuum filtration washed with 5 mL of MDC The filtrate was concentrated to dryness in vacuo

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

Procedure: 1-tridecanol; 1-tetradecanol; 1-pentadecanol; 1-hexadecanol;

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

Procedure: Pentadecyl acrylate was prepared by esterification of acrylic acid with 1-pentadecanol under standard conditions. Crude monomer was recrystallized from three volumes of ethanol and dried in vacuo. Ten grams of pentadecyl acrylate was dissolved in 20 ml of oxygen free ethylacetate containing 0.10 grams of azobis-isobutylnitrile (hereinafter AIBN) and stirred in a sealed bottle maintained at 60° C. for 24 hours. The resulting polymer was isolated by precipitation into cold ethanol and dried in vacuo. Analysis of the polymer showed it to have a first order transition temperature of 29° C., a heat of fusion of 59 J/g and a molecular weight of about 175,000 in an uncured state. Crude monomer was recrystallized from three volumes of ethanol dried in vacuo Ten grams of pentadecyl acrylate was dissolved in 20 ml of oxygen free ethylacetate containing 0.10 grams of azobis-isobutylnitrile (hereinafter AIBN) and The resulting polymer was isolated by precipitation into cold ethanol dried in vacuo a first order transition temperature of 29° C. a heat of fusion of 59 J/g

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

Procedure: 1-tridecanol; 1-tetradecanol; 1-pentadecanol; 1-hexadecanol;