反应详情

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.

1. filtrationThe crude product is filtered
2. washwashed with 1000 ml of isopropyl alcohol
3. customThe thus obtained wet solid is first recrystallized from 5000 ml of isopropyl alcohol
4. customdried in a vacuum oven at 65° to constant weight
5. customto give a white crystalline product, m.p. 154°-155°
6. customRecrystallization of 1781 g of the resulting salt from 9700 ml of anhydrous ethanol