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 621423ノート

反応式

HRID 621423 の反応式
[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

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178498981HCID 178498981、化合物

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-da8d2180e2fb43cea137a687186ac3ff
出典データセット
uspto-grants-1989_04
特許番号
US04824837

反応ノート

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