N-(3-HYDROXYPROPYL)ETHYLENEDIAMINE

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

Procedure: In 10 ml of methylene chloride was dissolved 10.4 g of N-(2-aminoethyl)propanolamine, and the solution was added to 15.0 g of [bis(methylthio)methylene]propanedinitrile. The mixture was allowed to stand at room temperature for 1 hour under reduced pressure. Diisopropyl ether was added to the mixture, and the solid was collected by filtration. The crystals were purified by silica gel column chromatography (chloroform:methanol=5:1) to give 15.0 g (87%) of Compound (VIa) as pale yellow crystals. the solid was collected by filtration The crystals were purified by silica gel column chromatography (chloroform:methanol=5:1)

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

Procedure: In 10 ml of methylene chloride was dissolved 10.4 g of N-(2-aminoethyl)propanolamine, and the solution was added to 15.0 g of [bis(methylthio)methylene]propanedinitrile. The mixture was allowed to stand at room temperature for 1 hour under reduced pressure. Diisopropyl ether was added to the mixture, and the solid was collected by filtration. The crystals were purified by silica gel column chromatography (chloroform:methanol=5:1) to give 15.0 g (87%) of Compound (VIa) as pale yellow crystals. the solid was collected by filtration The crystals were purified by silica gel column chromatography (chloroform:methanol=5:1)

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

Procedure: Into an apparatus similar to that in Example 1, were charged 118.2 g (1 mole) of N-hydroxypropylethylenediamine and 158.2 g (1 mole) of isopropyl 3-formyl-2-methylpropionate. From the apparatus, 18 g of water and 60 g of isopropyl alcohol were distilled off. Then, 340.5 g (1 mole) of behenic acid was charged and 18 g of water was distilled off at 180° C. and under a reduced pressure of 70 mmHg to obtain 4-behenoyloxypropyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one. From the apparatus, 18 g of water and 60 g of isopropyl alcohol were distilled off 18 g of water was distilled off at 180° C. and under a reduced pressure of 70 mmHg

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

Procedure: Into an apparatus similar to that in Example 1, were charged 118.2 g (1 mole) of N-hydroxypropylethylenediamine and 158.2 g (1 mole) of isopropyl 3-formyl-2-methylpropionate. From the apparatus, 18 g of water and 60 g of isopropyl alcohol were distilled off. Then, 340.5 g (1 mole) of behenic acid was charged and 18 g of water was distilled off at 180° C. and under a reduced pressure of 70 mmHg to obtain 4-behenoyloxypropyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one. From the apparatus, 18 g of water and 60 g of isopropyl alcohol were distilled off 18 g of water was distilled off at 180° C. and under a reduced pressure of 70 mmHg

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

Procedure: N-(3-hydroxypropyl)ethylenediamine (19.9 g, 168 mmol), DIPEA (87 mL, 504 mmol, 3.0 eq) were dissolved in 500 mL DMF, followed by the addition of 1,1-carbonyldiimidazole (27.3 g, 168 mmol, 1.0 eq). The reaction was allowed to stir at 50° C. overnight. After overnight, the reaction was cooled to room temperature and TBSCl (25.2 g, 168 mmol, 1.0 eq) was added. The mixture was allowed to stir at room temperature for 3 hours. The reaction was then condensed in vacuo at 40° C. and the obtained residue was then taken into DCM (500 mL). The organic phase was washed with water (2×500 mL) and then with brine (500 mL), dried over MgSO4, filtered and concentrated to afford the title compound as a light yellow solid (42.8 g) in 98% yield. After overnight the reaction was cooled to room temperature to stir at room temperature for 3 hours condensed in vacuo at 40° C. The organic phase was washed with water (2×500 mL) with brine (500 mL), dried over MgSO4 filtered concentrated

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

Procedure: N-(3-hydroxypropyl)ethylenediamine (19.9 g, 168 mmol), DIPEA (87 mL, 504 mmol, 3.0 eq) were dissolved in 500 mL DMF, followed by the addition of 1,1-carbonyldiimidazole (27.3 g, 168 mmol, 1.0 eq). The reaction was allowed to stir at 50° C. overnight. After overnight, the reaction was cooled to room temperature and TBSCl (25.2 g, 168 mmol, 1.0 eq) was added. The mixture was allowed to stir at room temperature for 3 hours. The reaction was then condensed in vacuo at 40° C. and the obtained residue was then taken into DCM (500 mL). The organic phase was washed with water (2×500 mL) and then with brine (500 mL), dried over MgSO4, filtered and concentrated to afford the title compound as a light yellow solid (42.8 g) in 98% yield. After overnight the reaction was cooled to room temperature to stir at room temperature for 3 hours condensed in vacuo at 40° C. The organic phase was washed with water (2×500 mL) with brine (500 mL), dried over MgSO4 filtered concentrated

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

Procedure: In 10 ml of methylene chloride was dissolved 10.4 g of N-(2-aminoethyl)propanolamine, and the solution was added to 15.0 g of [bis(methylthio)methylene]propanedinitrile. The mixture was allowed to stand at room temperature for 1 hour under reduced pressure. Diisopropyl ether was added to the mixture, and the solid was collected by filtration. The crystals were purified by silica gel column chromatography (chloroform:methanol=5:1) to give 15.0 g (87%) of Compound (VIa) as pale yellow crystals. the solid was collected by filtration The crystals were purified by silica gel column chromatography (chloroform:methanol=5:1)

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

Procedure: Into an apparatus similar to that in Example 1, were charged 118.2 g (1 mole) of N-hydroxypropylethylenediamine and 158.2 g (1 mole) of isopropyl 3-formyl-2-methylpropionate. From the apparatus, 18 g of water and 60 g of isopropyl alcohol were distilled off. Then, 340.5 g (1 mole) of behenic acid was charged and 18 g of water was distilled off at 180° C. and under a reduced pressure of 70 mmHg to obtain 4-behenoyloxypropyl-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one. From the apparatus, 18 g of water and 60 g of isopropyl alcohol were distilled off 18 g of water was distilled off at 180° C. and under a reduced pressure of 70 mmHg