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

HRID 449608ノート

反応式

HRID 449608 の反応式
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]

参加物

5

反応物 2

HCID 780131-IsopropylpiperazineHCID 8176205-Bromo-2-nitropyridine

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d84d17cbcbd2469093a892031e15f024
出典データセット
uspto-grants-2013_07
特許番号
US08481540B2

反応ノート

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