2-[(2-chlorophenoxy)methyl]oxirane

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:; See reaction.notes.procedure_details.

Procedure: 120 g of ethylenediamine are dissolved in 150 ml of ethanol. A solution of 20 g of o-chlorophenyl glycidyl ether ##STR18## in 40 ml of ethanol is added to the above solution, and the mixture is heated under reflux for 20 hours. Excess ethylenediamine and ethanol are then distilled off in vacuo, and the residue is then distilled in vacuo. The N-[3-(o-chlorophenoxy)-2-hydroxy-propyl]-ethylenediamine is thus obtained as an oil which can be distilled at a boiling point of 190° C./0.4 mm. The 4,5-dichloro-pyridazin-3-one used as the starting material is prepared in a known manner by the reaction of muccochloric acid with hydrazine (for example according to K. Dury, Angew. Chemie 77, page 282 (1965). the mixture is heated under reflux for 20 hours Excess ethylenediamine and ethanol are then distilled off in vacuo the residue is then distilled in vacuo

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

Procedure: A solution of 9.2 g of 1-(o-chloro-phenoxy)-2,3-epoxypropane and 9.15 g of 1-(4-piperidyl)-2-oxo-hexahydro-pyrimidine in 7 ml of abs. ethanol is heated for 5 hours to 95°C and then evaporated in vacuo. The residue is recrystallised from chloroform/petroleum ether to yield the 1-[3-(o-chloro-phenoxy)-2-hydroxypropyl]-4-(2-oxo-hexahydro-1-pyrimidinyl)-piperidine, which melts at 150°-153°C. evaporated in vacuo The residue is recrystallised from chloroform/petroleum ether

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

Procedure: Using the method of Example 25, supra, 2-chlorophenyl glycidyl ether (1.0 mmol) and 1,1-dimethyl-2-(4-methoxyphenyl)ethylamine (1.25 mmol) yielded 279 mg of the title compound as a white solid: GC/EI-MS, m/z (rel. int.) 348 (M-15, 5), 245 (21), 244 (100), 242 (100), 163 (29), 121 (82), 114 (24), 77 (21), 71 (44), 70 (56), 58 (24).

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

Procedure: Using the method of Example 25, supra, 2-chlorophenyl glycidyl ether (1.0 mmol) and 1,1-dimethyl-2-(4-methoxyphenyl)ethylamine (1.25 mmol) yielded 279 mg of the title compound as a white solid: GC/EI-MS, m/z (rel. int.) 348 (M-15, 5), 245 (21), 244 (100), 242 (100), 163 (29), 121 (82), 114 (24), 77 (21), 71 (44), 70 (56), 58 (24).

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

Procedure: A solution of 9.2 g of 1-(o-chloro-phenoxy)-2,3-epoxy-propane and 9.15 g of 1-(4-piperidyl)-2-oxo-hexahydro-pyrimidine in 7 ml of abs. ethanol is heated for 5 hours to 95° C and then evaporated in vacuo. The residue is recrystallised from chloroform/petroleum ether to yield the 1-[3-(o-chloro-phenoxy)-2-hydroxypropyl]-4-(2-oxo-hexahydro-1-pyrimidinyl)-piperidine, which melts at 150°-153° C. evaporated in vacuo The residue is recrystallised from chloroform/petroleum ether

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

Procedure: A solution of 9.2 g of 1-(o-chloro-phenoxy)-2,3-epoxypropane and 9.15 g of 1-(4-piperidyl)-2-oxo-hexahydro-pyrimidine in 7 ml of abs. ethanol is heated for 5 hours to 95° C and then evaporated in vacuo. The residue is recrystallised from chloroform/petroleum ether to yield the 1-[3-(o-chloro-phenoxy)-2-hydroxypropyl]-4-(2-oxo-hexahydro-1-pyrimidinyl)-piperidine, which melts at 150°-153° C. evaporated in vacuo The residue is recrystallised from chloroform/petroleum ether

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

Procedure: 120 g of ethylenediamine are dissolved in 150 ml of ethanol. A solution of 20 g of o-chlorophenyl glycidyl ether ##STR18## in 40 ml of ethanol is added to the above solution, and the mixture is heated under reflux for 20 hours. Excess ethylenediamine and ethanol are then distilled off in vacuo, and the residue is then distilled in vacuo. The N-[3-(o-chlorophenoxy)-2-hydroxy-propyl]-ethylenediamine is thus obtained as an oil which can be distilled at a boiling point of 190° C./0.4 mm. The 4,5-dichloro-pyridazin-3-one used as the starting material is prepared in a known manner by the reaction of muccochloric acid with hydrazine (for example according to K. Dury, Angew. Chemie 77, page 282 (1965). the mixture is heated under reflux for 20 hours Excess ethylenediamine and ethanol are then distilled off in vacuo the residue is then distilled in vacuo

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

Procedure: 120 g of ethylenediamine are dissolved in 150 ml of ethanol. A solution of 20 g of o-chlorophenyl glycidyl ether ##STR18## in 40 ml of ethanol is added to the above solution, and the mixture is heated under reflux for 20 hours. Excess ethylenediamine and ethanol are then distilled off in vacuo, and the residue is then distilled in vacuo. The N-[3-(o-chlorophenoxy)-2-hydroxy-propyl]-ethylenediamine is thus obtained as an oil which can be distilled at a boiling point of 190° C./0.4 mm. The 4,5-dichloro-pyridazin-3-one used as the starting material is prepared in a known manner by the reaction of muccochloric acid with hydrazine (for example according to K. Dury, Angew. Chemie 77, page 282 (1965). the mixture is heated under reflux for 20 hours Excess ethylenediamine and ethanol are then distilled off in vacuo the residue is then distilled in vacuo