propane-1,2-diamine

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

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

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

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

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

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Equimolar amounts of N-allyl, N-methyl, propylene diamine prepared as described above and Dimethyl Itaconate are charged to a reaction vessel and heated slowly with agitation to 130°-150° C. After the exotherm subsides, the reaction mixture is maintained at 140° C. for 3 hours. The reaction product 1-(N-allyl, N-methyl aminopropyl)-4-carbomethoxy pyrrolidone is isolated by distillation. are charged to a reaction vessel heated slowly with agitation to 130°-150° C

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

Procedure: To a stirred solution of p-toluenesulfonyl chloride (270 g, 1.42 mole) and triethylamine (143 g, 1.42 mole) in CH2Cl2 (1.0 l) at 0° C. under a dry argon atmosphere was added a solution of 1,2-diaminopropane (50.0 g, 0.675 mole) in CH2Cl2 (250 ml) dropwise, maintaining the temperature <10° C. The addition required 1 h. The mixture was allowed to warm to room temperature and was stirred an additional 19 h. The mixture was poured onto ice (1000 g) and the CH2Cl2 layer was separated. The CH2Cl2 layer was washed with 1N HCl, H2O and saturated NaCl solution and was dried (MgSO4). The solvent was removed in vacuo and the resulting yellow oil was washed with hexane. The crude product was purified by recrystallization from CH2Cl2 -hexane to give 241 g (93% yield) of the product as colorless needles: mp 105°-7° C.; 1H NMR(CDC13) δ 0.97 (d, J=6.7 Hz, 3 H), 2.40 (s, 3 H), 2.41 (s, 3 H), 2.91 (m, 2 H), 3.32 (m, 1 H), 5.25 (d, J=7.6 Hz, 1 H), 5.38 (t, J=6.3 Hz, 1 H), 7.28 (m, 4 H) 7.73, (m, 4 H). maintaining the temperature <10° C The addition required 1 h The mixture was poured onto ice (1000 g) the CH2Cl2 layer was separated The CH2Cl2 layer was washed with 1N HCl, H2O and saturated NaCl solution was dried (MgSO4) The solvent was removed in vacuo the resulting yellow oil was washed with hexane The crude product was purified by recrystallization from CH2Cl2 -hexane

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

Procedure: In a manner analogous to that described in U.S. Pat. No. 2,920,077, 148.3 g (2 moles) of 1,2-diaminopropane and about 500 ml water are placed in a 2-liter 3-necked flask. While stirring, 170.2 g (2moles) of acetone cyanohydrin in 100 ml water are added in 20 min. The reaction is allowed to proceed at 80°-92° C. for 24 hr then water and unreacted materials are removed at 15 mm Hg. The residue, which formed a solid on standing, when dissolved in acetone and recrystallized was found to melt at 115°-117°. water and unreacted materials are removed at 15 mm Hg The residue, which formed a solid recrystallized to melt at 115°-117°

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

Procedure: First, with 150 mL of dehydrated ethanol as a solvent, 5.07 g of 4,4′-bis(trifluoromethyl)benzil and 1.09 g of 1,2-diaminopropane were mixed, and the mixture was refluxed in a nitrogen atmosphere for four hours. After reaction, a reaction solution was condensed under reduced pressure, and an obtained residue was recrystallized by using ethanol to obtain 2-methyl-5,6-bis(4-trifluoromethylphenyl)-2,3-dihydropyrazine (light yellow crystal, yield: 87%). Further, with 100 mL of dehydrated ethanol as a solvent, 5.05 g of 2-methyl-5,6-bis(4-trifluoromethylphenyl)-2,3-dihydropyrazine that is obtained as described above and 4.26 g of iron (III) chloride were mixed, and the mixture was heated in a nitrogen atmosphere for two hours in a gentle manner. After reaction, water was added into a reaction solution for dilution, and extraction was performed with ether. An extraction solution was dried with magnesium sulfate and filtered, and solvent of filtrate was removed. An obtained residue was recrystallized with ethanol to obtain 5-methyl-2,3-bis(4-trifluoromethylphenyl)pyrazine (CF3DPPR-Me) that is a ligand (white powder, yield: 52%). A synthesis scheme (h-1) relating to the synthesis of Step 1 is shown below. the mixture was refluxed in a nitrogen atmosphere for four hours After reaction condensed under reduced pressure an obtained residue was recrystallized

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

Procedure: First, with ethanol as a solvent, 5.31 g of 4,4′-difluorobenzil (by Tokyo Chemical Industry Co., Ltd.) and 1.60 g of 1,2-diaminopropane (by Tokyo Chemical Industry Co., Ltd.) were mixed, and the mixture was refluxed for three hours. After reaction, a reaction solution was condensed by using an evaporator, and an obtained residue was recrystallized by using ethanol; thus, 2,3-bis(4-fluorophenyl)-5-methyl-5,6-dihydropyrazine was obtained (light yellow powder, yield: 86%). the mixture was refluxed for three hours After reaction condensed an evaporator an obtained residue was recrystallized

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

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