3-Bromo-4-nitropyridine N-oxide → 1-(4-Nitro-1-oxido-pyridin-1-ium-3-yl)-4-(oxetan-3-yl)piperazine

HRID 1850683ノート

反応式

HRID 1850683 の反応式
Br[C:2]1[CH:3]=[N+:4]([O-:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[O:12]1[CH2:15][CH:14]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:13]1>CCO>[N+:8]([C:7]1[CH:6]=[CH:5][N+:4]([O-:11])=[CH:3][C:2]=1[N:19]1[CH2:20][CH2:21][N:16]([CH:14]2[CH2:15][O:12][CH2:13]2)[CH2:17][CH2:18]1)([O-:10])=[O:9]

参加物

4

反応物 2

HCID 5485213-Bromo-4-nitropyridine N-oxideHCID 574162871-(Oxetan-3-yl)piperazine

生成物 1

HCID 904113171-(4-Nitro-1-oxido-pyridin-1-ium-3-yl)-4-(oxetan-3-yl)piperazine収率 86.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 3-bromo-4-nitro-1-oxido-pyridin-1-ium (500 mg, 2.283 mmol) and 1-(oxetan-3-yl)piperazine (649.3 mg, 4.566 mmol) in EtOH (10 mL) were heated at reflux for 17 hours. The reaction was cooled to ambient temperature and the solvent removed in vacuo. The residue was passed through a 25 g SCX-2 cartridge (pre-wetted with MeOH), eluting with 2M NH3 in MeOH/DCM. The solvents were removed in vacuo and the residue purified by column chromatography (ISCO Companion, 40 g column, eluting with 0 to 10% MeOH/DCM, loaded in DCM) to give 1-(4-nitro-1-oxido-pyridin-1-ium-3-yl)-4-(oxetan-3-yl)piperazine as an orange solid (553 mg, 86% Yield).

後処理

  1. temperaturewere heated
  2. temperatureat reflux for 17 hours
  3. customthe solvent removed in vacuo
  4. washeluting with 2M NH3 in MeOH/DCM
  5. customThe solvents were removed in vacuo
  6. customthe residue purified by column chromatography (ISCO Companion, 40 g column, eluting with 0 to 10% MeOH/DCM, loaded in DCM)

出典と根拠

ORDレコード
ord-2b593e8115fd41b28ce11a2f4792a387
出典データセット
uspto-grants-2015_02
特許番号
US08957078B2

反応ノート

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