1-Isopropylpiperazine → 1-Isopropyl-4-(6-nitropyridin-3-yl)piperazine

HRID 449608노트

반응식

HRID 449608 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[CH:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:13])[CH3:12]>CS(C)=O.O>[CH:11]([N:14]1[CH2:19][CH2:18][N:17]([C:2]2[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:16][CH2:15]1)([CH3:13])[CH3:12]

참가 물질

5

반응물 2

HCID 780131-IsopropylpiperazineHCID 8176205-Bromo-2-nitropyridine

생성물 1

HCID 575020971-Isopropyl-4-(6-nitropyridin-3-yl)piperazine수율 64%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

To 5-bromo-2-nitropyridine (1.0 g, 4.93 mmol, Eq: 1.00) in DMSO (10.0 ml) was added 1-isopropylpiperazine (632 mg, 4.93 mmol, Eq: 1.00), and the resulting solution was heated at 70° C. for 18 hours. The solution was cooled to room temperature. The solution was diluted with 50 ml water. The resulting solid was filtered. The solid was washed with water and dried under vacuum. The crude material was purified by flash chromatography (silica gel, 80 g, 0% to 3% MeOH/DCM gradient) to give 1-isopropyl-4-(6-nitropyridin-3-yl)piperazine (788 mg, 64%). LC/MS-ESI observed [M+H]+ 251.

후처리

  1. temperatureThe solution was cooled to room temperature
  2. filtrationThe resulting solid was filtered
  3. washThe solid was washed with water
  4. customdried under vacuum
  5. customThe crude material was purified by flash chromatography (silica gel, 80 g, 0% to 3% MeOH/DCM gradient)

출처 및 근거

ORD 기록
ord-d84d17cbcbd2469093a892031e15f024
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481540B2

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