2-[(2-prop-2-enoxyphenoxy)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:; See reaction.notes.procedure_details.

Procedure: A solution of 10.3 g of 1-(o-allyloxy-phenoxy)-2,3-epoxy-propane and 9.15 g of 1-(4-piperidyl)-2-oxo-hexahydro-pyrimidine in 7 ml abs. ethanol is heated for 5 hours to 95°C and then evaporated in vacuo. The residue is recrystallised from isopropanol to yield the 1-[3-(o-allyloxy-phenoxy)-2-hydroxypropyl]-4-(2-oxo-hexahydro-1-pyrimidinyl)piperidine, which melts at 122°-125°C. evaporated in vacuo The residue is recrystallised from isopropanol

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

Procedure: A mixture of 657.6 g of 92% pure o-(allyloxy)phenoxymethyloxirane (U.S. Pat. No. 3,483,221) and 512 g of cis-1-(4-aminocyclohexyl)-2-imidazolidinone is stirred and refluxed for 6 hours in 6,000 ml of isopropanol. To the above reaction mixture, while still hot, is added 162.1 g of fumaric acid. The resulting mixture is allowed to stir at room temperature overnight. The crude product is filtered and washed with 1000 ml of isopropyl alcohol. The thus obtained wet solid is first recrystallized from 5000 ml of isopropyl alcohol and then dried in a vacuum oven at 65° to constant weight to give a white crystalline product, m.p. 154°-155°. Recrystallization of 1781 g of the resulting salt from 9700 ml of anhydrous ethanol yields cis-1-{4-[3-(o-allyloxyphenoxy)-2-hydroxypropylamino]-cyclohexyl}-2-imidazolidinone hemifumarate salt, m.p. 156°-7°, being the cis compound of formula III wherein R3 represents hydrogen and R7 represents allyloxy, as the hemifumarate salt. The crude product is filtered washed with 1000 ml of isopropyl alcohol The thus obtained wet solid is first recrystallized from 5000 ml of isopropyl alcohol dried in a vacuum oven at 65° to constant weight to give a white crystalline product, m.p. 154°-155° Recrystallization of 1781 g of the resulting salt from 9700 ml of anhydrous ethanol

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

Procedure: A mixture of 657.6 g of 92% pure o-(allyloxy)phenoxymethyloxirane (U.S. Pat. No. 3,483,221) and 512 g of cis-1-(4-aminocyclohexyl)-2-imidazolidinone is stirred and refluxed for 6 hours in 6,000 ml of isopropanol. To the above reaction mixture, while still hot, is added 162.1 g of fumaric acid. The resulting mixture is allowed to stir at room temperature overnight. The crude product is filtered and washed with 1000 ml of isopropyl alcohol. The thus obtained wet solid is first recrystallized from 5000 ml of isopropyl alcohol and then dried in a vacuum oven at 65° to constant weight to give a white crystalline product, m.p. 154°-155°. Recrystallization of 1781 g of the resulting salt from 9700 ml of anhydrous ethanol yields cis-1-{4-[3-(o-allyloxyphenoxy)-2-hydroxypropylamino]-cyclohexyl}-2-imidazolidinone hemifumarate salt, m.p. 156°-7°, being the cis compound of formula III wherein R3 represents hydrogen and R7 represents allyloxy, as the hemifumarate salt. The crude product is filtered washed with 1000 ml of isopropyl alcohol The thus obtained wet solid is first recrystallized from 5000 ml of isopropyl alcohol dried in a vacuum oven at 65° to constant weight to give a white crystalline product, m.p. 154°-155° Recrystallization of 1781 g of the resulting salt from 9700 ml of anhydrous ethanol

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

Procedure: Prepared analogously to Example 1 from 1-(2-allyloxy-phenoxy)-2,3-epoxypropane and 6-[2-(2-aminoethyl)benzimidazol-5-yl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone.

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

Procedure: Prepared analogously to Example 1 from 1-(2-allyloxy-phenoxy)-2,3-epoxypropane and 6-[2-(2-aminoethyl)benzimidazol-5-yl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone.

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

Procedure: Prepared analogously to Example 1 from 1-(2-allyloxy-phenoxy)-2,3-epoxypropane and 6-[2-(2-aminoethyl)benzimidazol-5-yl]-4,5-dihydro-3(2H)-pyridazinone.

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

Procedure: Prepared analogously to Example 1 from 1-(2-allyloxy-phenoxy)-2,3-epoxypropane and 6-[2-(2-aminoethyl)benzimidazol-5-yl]-4,5-dihydro-3(2H)-pyridazinone.

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

Procedure: Prepared analogously to Example 1 from 1-(2-allyloxy-phenoxy)-2,3-epoxypropane and 6-[3-(2-aminoethoxy)phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone.

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

Procedure: Prepared analogously to Example 1 from 1-(2-allyloxy-phenoxy)-2,3-epoxypropane and 6-[4-(2-aminoethoxy)phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone.