Hydrochloric Acid → 1-Methyl-4-(6-nitropyridin-3-yl)piperazine

HRID 68439

반응식

HRID 68439 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.Cl>CS(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([C:2]2[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:20][CH2:19]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 8176205-Bromo-2-nitropyridine

생성물 1

HCID 517114841-Methyl-4-(6-nitropyridin-3-yl)piperazine수율 83.1%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
120 °C

실험 절차

To 5-Bromo-2-nitro-pyridine (2.00 g, 9.85 mmol) in 10 mL dimethylsulfoxide was added potassium carbonate (2.72 g, 19.7 mmol), 1-methylpiperazine (1.64 mL, 14.8 mmol), and tetrabutylammonium iodide (36 mg, 0.097 mmol) and was heated at 120° C. for 18 hours. The mixture was made acidic with 1M aq. HCl and was partitioned between dichloromethane and water. The aqueous layer was made basic with 2M aq. sodium carbonate and was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, concentrated in vacuo, and was triturated with water to yield 1-Methyl-4-(6-nitro-pyridin-3-yl)-piperazine (1.82 g, 8.19 mmol). MS (ESI) 223.1 (M+H)+.

후처리

  1. customwas partitioned between dichloromethane and water
  2. extractionwas extracted with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customwas triturated with water

출처 및 근거

ORD 기록
ord-39e811d8cd514cef8227c892e3909540
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822457B2

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