Fumaric Acid → HCID 178458334, compound

HRID 979884Notes

Reaction equation

HRID 979884 reaction equation
[CH2:1]([O:4][C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH2:8][CH:9]1[CH2:11][O:10]1)[CH:2]=[CH2:3].[NH2:16][C@@H:17]1[CH2:22][CH2:21][C@H:20]([N:23]2[CH2:27][CH2:26][NH:25][C:24]2=[O:28])[CH2:19][CH2:18]1.[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33]>C(O)(C)C>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33].[CH2:1]([O:4][C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH2:8][CH:9]([OH:10])[CH2:11][NH:16][C@@H:17]1[CH2:18][CH2:19][C@H:20]([N:23]2[CH2:27][CH2:26][NH:25][C:24]2=[O:28])[CH2:21][CH2:22]1)[CH:2]=[CH2:3].[CH2:1]([O:4][C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH2:8][CH:9]([OH:10])[CH2:11][NH:16][C@@H:17]1[CH2:18][CH2:19][C@H:20]([N:23]2[CH2:27][CH2:26][NH:25][C:24]2=[O:28])[CH2:21][CH2:22]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 444972Fumaric AcidHCID 5743337[[o-(Allyloxy)phenoxy]methyl]oxiraneHCID 178511575HCID 178511575, compound

Product 1

HCID 178458334HCID 178458334, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

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.

Workup

  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

Sources & evidence

ORD record
ord-7761441417774a2e89326b411db922f7
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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