Fumaric Acid → HCID 178525527, compound

HRID 979900Notes

Reaction equation

HRID 979900 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][NH:10][C:9]2=[O:13])[CH2:4][CH2:3]1.[CH:14]1([CH2:17][O:18][C:19]2[CH:29]=[CH:28][C:22]([O:23][CH2:24][CH:25]3[CH2:27][O:26]3)=[CH:21][CH:20]=2)[CH2:16][CH2:15]1.[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34]>C(O)(C)C>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34].[CH:14]1([CH2:17][O:18][C:19]2[CH:29]=[CH:28][C:22]([O:23][CH2:24][CH:25]([OH:26])[CH2:27][NH:1][C@@H:2]3[CH2:3][CH2:4][C@H:5]([N:8]4[CH2:12][CH2:11][NH:10][C:9]4=[O:13])[CH2:6][CH2:7]3)=[CH:21][CH:20]=2)[CH2:16][CH2:15]1.[CH:14]1([CH2:17][O:18][C:19]2[CH:29]=[CH:28][C:22]([O:23][CH2:24][CH:25]([OH:26])[CH2:27][NH:1][C@@H:2]3[CH2:3][CH2:4][C@H:5]([N:8]4[CH2:12][CH2:11][NH:10][C:9]4=[O:13])[CH2:6][CH2:7]3)=[CH:21][CH:20]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 444972Fumaric AcidHCID 20223083p-(Cyclopropylmethoxy)-phenoxymethyloxiraneHCID 178511575HCID 178511575, compound

Product 1

HCID 178525527HCID 178525527, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 3.7 g of cis 1-(4-aminocyclohexyl)-2-imidazolidinone and 4.7 g of p-(cyclopropylmethoxy)-phenoxymethyloxirane in 50 ml of isopropanol is stirred at reflux for 6 hours. After standing at room temperature 16 hours, the solution is treated with 1.17 g of fumaric acid and heated at reflux for 30 minutes. A solid precipitates, the reaction mixture is cooled to room temperature, the product is filtered off, washed with isopropanol, and dried in vacuo at 65° to yield cis-1-{4-[3-(p-cyclopropylmethoxyphenoxy)-2-hydroxypropylamino]-cyclohexyl}-2-imidazolidone hemifumarate, m.p. 163°-165°.

Workup

  1. temperatureat reflux for 6 hours
  2. temperatureheated
  3. temperatureat reflux for 30 minutes
  4. customA solid precipitates
  5. filtrationthe product is filtered off
  6. washwashed with isopropanol
  7. customdried in vacuo at 65°

Sources & evidence

ORD record
ord-1eb9c1c694234287a1eb4088fe4c28b4
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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