Ethanol → HCID 20262853, compound

HRID 464253Notes

Reaction equation

HRID 464253 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH:13]=[C:12]([CH3:14])[NH:11][CH:10]([CH2:15][O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:9]1([C:29]([O:31][CH2:32][CH3:33])=[O:30])C(OC)=O.[C:34]([OH:39])(=[O:38])C(O)=O.C(O[C:43]1[NH:44][CH2:45][CH2:46][CH:47]=1)C.[CH2:48](O)C>>[N:44]1[CH2:45][CH2:46][CH2:47][C:43]=1[N:22]1[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][O:16][CH2:15][C:10]2[NH:11][C:12]([CH3:14])=[C:13]([C:34]([O:39][CH3:48])=[O:38])[CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:9]=2[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:24][CH2:23]1

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 971Oxalic AcidHCID 15426392HCID 15426392, compoundHCID 20262851HCID 20262851, compound

Product 1

HCID 20262853HCID 20262853, compound

Procedure

4-(2-Chlorophenyl)-3-(ethoxycarbonyl)-3-(methoxycarbonyl)-6-methyl-2-[2-(piperazin-1-yl)ethoxymethyl]-1,4-dihydropyridine (0.7 g) was dissolved in 10 ml of ethanol and converted to the oxalate salt by addition of a solution of 0.15 g of oxalic acid in 5 ml of ethanol. To this suspension was added 0.12 g of 2-ethoxypyrroline and the mixture was refluxed for 18 hours. The reaction mixture was then filtered through "Solka-floc" (Trade Mark) and evaporated to dryness. The resultant solid was basified with aqueous sodium carbonate solution and extracted with methylene chloride to give a white solid. After two crystallizations from diisopropylether, there was obtained 0.1 g of the title compound, m.p. 104°.

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. filtrationThe reaction mixture was then filtered through "Solka-floc" (Trade Mark)
  3. customevaporated to dryness
  4. extractionextracted with methylene chloride
  5. customto give a white solid
  6. customAfter two crystallizations from diisopropylether

Sources & evidence

ORD record
ord-1db1243a7fb042ec9ab81c5a27b855a0
Source dataset
uspto-grants-1985_10
Patent number
US04547502

Reaction notes

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