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Phenyl glycidyl ether → Diethyl 2-ethyl-4-[2-[4-(2-hydroxy-3-phenoxypropylamino)butoxy]-5-nitrophenyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 4667
Notes
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Reaction equation

HRID 4667 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[CH:16]1[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:20]([CH3:27])[NH:19][C:18]([CH2:28][CH3:29])=[C:17]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].[C:35]1([O:41][CH2:42][CH:43]2[O:45][CH2:44]2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CO>[CH2:28]([C:18]1[NH:19][C:20]([CH3:27])=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:16]([C:8]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][CH2:44][CH:43]([OH:45])[CH2:42][O:41][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:17]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 31217Phenyl glycidyl etherHCID 14050495Diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2-ethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 14050483Diethyl 2-ethyl-4-[2-[4-(2-hydroxy-3-phenoxypropylamino)butoxy]-5-nitrophenyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylateYield 20.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 46 ml of methanol were dissolved 4.62 g of diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2-ethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate and 1.46 g of glycidyl phenyl ether, and the solution formed was refluxed under heating for 15 hours. After cooling the reaction solution, the solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the product was eluted with chloroform-methanol (95:5 v/v). Crude crystals were recrystallized from ethanol to give 1.22 g of diethyl 2-ethyl-4-[2-[4-(2-hydroxy-3-phenoxypropylamino)butoxy]-5-nitrophenyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate.

Workup

  1. customthe solution formed
  2. temperaturewas refluxed
  3. temperatureunder heating for 15 hours
  4. temperatureAfter cooling the reaction solution
  5. concentrationthe solution was concentrated under reduced pressure
  6. washthe product was eluted with chloroform-methanol (95:5 v/v)
  7. customCrude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-2f3c02f79686496e8840329c81d3621d
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04727082

Reaction notes

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