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

HRID 1850683노트

반응식

HRID 1850683 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2b593e8115fd41b28ce11a2f4792a387
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957078B2

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