Phenyl glycidyl ether → HCID 23359374, compound

HRID 1195142Notes

Reaction equation

HRID 1195142 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-4cc3b12fe9ba49a998085e3c5d04f333
Source dataset
uspto-grants-1992_05
Patent number
US05110820

Reaction notes

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