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

HRID 4664

Reaction equation

HRID 4664 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]([CH3:28])=[C:17]1[C:29]([O:31][CH2:32][CH3:33])=[O:30].[C:34]1([O:40][CH2:41][CH:42]2[O:44][CH2:43]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CO>[OH:44][CH:42]([CH2:41][O:40][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:43][NH: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]([CH3:28])=[C:17]1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

4

Reactant 2

HCID 31217Phenyl glycidyl etherHCID 20151528Diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 14050446Diethyl 4-[2-[4-(2-hydroxy-3-phenoxypropylamino)butoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateYield 31.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 500 ml of methanol were dissolved 5.2 g of diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 1.7 g of glycidyl phenyl ether, and the solution thus formed was refluxed under heating for 16 hours. The solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography, and the product was eluted with chlroform-methanol (95:5 v/v). Crude crystals were recrystallized from ethanol to give 2.2 g of diethyl 4-[2-[4-(2-hydroxy-3-phenoxypropylamino)butoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate.

Workup

  1. customthe solution thus formed
  2. temperaturewas refluxed
  3. temperatureunder heating for 16 hours
  4. distillationThe solvent was distilled off under reduced pressure
  5. washthe product was eluted with chlroform-methanol (95:5 v/v)
  6. customCrude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-f7d6b5a0a92348dbad2bb63286d5a2ea
Source dataset
uspto-grants-1988_02
Patent number
US04727082

Linked notes

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