Potassium Carbonate → 1-(4-Methoxyphenyl)-4-(5-nitro-2-pyridinyl)piperazine

HRID 266062

반응식

HRID 266062 반응식
Cl.Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.Cl[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=3)[CH2:13][CH2:12]2)=[CH:9][CH:10]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 27237001-(4-Methoxyphenyl)-piperazine, dihydrochloride

생성물 1

HCID 37426761-(4-Methoxyphenyl)-4-(5-nitro-2-pyridinyl)piperazine수율 57.4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
140 °C

실험 절차

A mixture of 36 g of 1-(4-methoxyphenyl)piperazine dihydrochloride, 22 g of 2-chloro-5-nitropyridine, 58 g of potassium carbonate and 227 ml of dimethyl sulfoxide was stirred overnight at 140° C. The reaction mixture was cooled and poured onto water. The precipitated product was filtered off, washed with water and dissolved in dichloromethane. The solution was treated with activated charcoal. The latter is filtered off and the filtrate was evaporated. The residue was triturated in 2-propanol. The product was filtered off and crystallized from 1-butanol, yielding 24.5 g of 1-(4-methoxyphenyl)-4-(5-nitro-2-pyridinyl)piperazine; mp. 170° C. (interm. 21).

후처리

  1. temperatureThe reaction mixture was cooled
  2. additionpoured onto water
  3. filtrationThe precipitated product was filtered off
  4. washwashed with water
  5. dissolutiondissolved in dichloromethane
  6. additionThe solution was treated with activated charcoal
  7. filtrationThe latter is filtered off
  8. customthe filtrate was evaporated
  9. customThe residue was triturated in 2-propanol
  10. filtrationThe product was filtered off
  11. customcrystallized from 1-butanol

출처 및 근거

ORD 기록
ord-0a116ba728584cf7b32d9a1d3add1357
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650411

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