Phenyl glycidyl ether → HCID 23359374, compound

HRID 232699Notes

Reaction equation

HRID 232699 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:30])=[C:5]([C:26]([O:28][CH3:29])=[O:27])[CH:6]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][NH2:16])=[O:9].[C:31]1([O:37][CH2:38][CH:39]2[O:41][CH2:40]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(O)C>[CH3:1][C:2]1[NH:3][C:4]([CH3:30])=[C:5]([C:26]([O:28][CH3:29])=[O:27])[CH:6]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][NH:16][CH2:40][CH:39]([OH:41])[CH2:38][O:37][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:9]

Participants

4

Reactant 2

HCID 31217Phenyl glycidyl etherHCID 23359386HCID 23359386, compound

Product 1

HCID 23359374HCID 23359374, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 20 ml of ethanol were dissolved 1.8 g of 2-(2-aminoethoxy)ethyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate and 0.64 g of glycidyl phenyl ether, and the solution was stirred at room temperature for 20 hours. The reaction solution was concentrated under reduced pressure and the residue was subjected to silica gel column chromatography. The product was eluted with chloroform-methanol (95.5 v/v), and 0.87 g of 2-[2-(2-hydroxy-3-phenoxypropylamino)ethoxy]ethyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate was obtained. The product was treated with an ethanol solution of hydrochloric acid to provide 0.8 g of hydrochloric acid salt as amorphous powder.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. washThe product was eluted with chloroform-methanol (95.5 v/v)

Sources & evidence

ORD record
ord-708cf32605344703ba1c75b26a002fd4
Source dataset
uspto-grants-1997_01
Patent number
US05591757

Reaction notes

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