Phenyl glycidyl ether → HCID 23359377, compound

HRID 232700Notes

Reaction equation

HRID 232700 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:32])=[C:5]([C:28]([O:30][CH3:31])=[O:29])[CH:6]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[O:9].[C:33]1([O:39][CH2:40][CH:41]2[O:43][CH2:42]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CO>[CH3:1][C:2]1[NH:3][C:4]([CH3:32])=[C:5]([C:28]([O:30][CH3:31])=[O:29])[CH:6]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][CH2:42][CH:41]([OH:43])[CH2:40][O:39][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:9]

Participants

4

Reactant 2

HCID 31217Phenyl glycidyl etherHCID 13752660HCID 13752660, compound

Product 1

HCID 23359377HCID 23359377, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 45 ml of methanol were dissolved 2.51 g of 6-aminohexyl methyl 2,6-dimethyl-4-(m-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate and 0.83 g of glycidyl phenyl ether, and the mixture was stirred for 45 hours at room temperature. The reaction solution was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography. The produce was eluted with chloroform-methanol (95:5 v/v), and 1.10 g of 6-(2-hydroxy-3-phenoxypropylamino)hexyl methyl 2,6-dimethyl-4-(m-trifluoromethylphenyl)-1,4-dihydropyridin-3,5-dicarboxylate was obtained. This product was treated with an ethanol solution of hydrogen chloride to obtain amorphous powder of 1.16 g of hydrochloric acid salt.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. washThe produce was eluted with chloroform-methanol (95:5 v/v)

Sources & evidence

ORD record
ord-88955fad3b224f348513af35d5cddaed
Source dataset
uspto-grants-1997_01
Patent number
US05591757

Reaction notes

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