Phosphorus oxychloride → 5-{2-[4-(Diphenylmethyl)piperazin-1-yl]ethyl} 3-methyl 2-chloro-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 621423Notes

Reaction equation

HRID 621423 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][O:22][C:23]([C:25]2[CH:26]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([N+:43]([O-:45])=[O:44])[CH:38]=3)[C:27]([C:33]([O:35][CH3:36])=[O:34])=[C:28](O)[NH:29][C:30]=2[CH3:31])=[O:24])[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:48])=O>>[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][O:22][C:23]([C:25]2[CH:26]([C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([N+:43]([O-:45])=[O:44])[CH:38]=3)[C:27]([C:33]([O:35][CH3:36])=[O:34])=[C:28]([Cl:48])[NH:29][C:30]=2[CH3:31])=[O:24])[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178498981HCID 178498981, compound

Product 1

HCID 30652925-{2-[4-(Diphenylmethyl)piperazin-1-yl]ethyl} 3-methyl 2-chloro-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateYield 57.2%

Procedure

5-[2-(4-Benzhydrylpiperazin-1-yl)ethyl]oxycarbonyl-2-hydroxy-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine (390 mg) was dissolved in phosphorus oxychloride (5 ml) and the mixture was heated under reflux for 3 hours and 10 minutes. After excess phosphorus oxychloride had been distilled off under reduced pressure, the reaction mixture was diluted with saturated potassium carbonate and subjected to extraction with chloroform. The extract was distilled off and the residue was subjected to silica gel column chromatography (elution solvent: 1% chloroform/methanol), thereby obtaining crude crystals. This crude crystals were recrystallized from a solution of chloroform/isopropylether/hexane to yield 210 mg (57.2%) of the desired compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours and 10 minutes
  3. distillationAfter excess phosphorus oxychloride had been distilled off under reduced pressure
  4. additionthe reaction mixture was diluted with saturated potassium carbonate
  5. extractionsubjected to extraction with chloroform
  6. distillationThe extract was distilled off
  7. washthe residue was subjected to silica gel column chromatography (elution solvent: 1% chloroform/methanol)
  8. customobtaining crude crystals
  9. customThis crude crystals were recrystallized from a solution of chloroform/isopropylether/hexane

Sources & evidence

ORD record
ord-da8d2180e2fb43cea137a687186ac3ff
Source dataset
uspto-grants-1989_04
Patent number
US04824837

Reaction notes

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