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 621423노트

반응식

HRID 621423 반응식
[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

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178498981HCID 178498981, 화합물

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-da8d2180e2fb43cea137a687186ac3ff
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04824837

반응 노트

불러오는 중…