Piperazine → 1-(3-Chloro-5-fluoro-4-pyridyl)piperazine

HRID 524873노트

반응식

HRID 524873 반응식
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:9])[C:7]=1I.CCN(C(C)C)C(C)C.[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:9])[C:7]=1[N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1

참가 물질

5

반응물 3

HCID 4837PiperazineHCID 81531DiisopropylethylamineHCID 110325453-Chloro-5-fluoro-4-iodopyridine

생성물 1

HCID 867209301-(3-Chloro-5-fluoro-4-pyridyl)piperazine

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

In a 100 mL sealed reaction vessel/bomb, 3-chloro-5-fluoro-4-iodo-pyridine (5600 mg, 21.75 mmol) was taken up in NMP (12 mL). To the resulting clear brown solution was added DIPEA (3.373 g, 4.546 mL, 26.10 mmol) followed by piperazine (2.810 g, 32.62 mmol). The vessel was sealed and heated thermally at 120° C. for 18 hrs. The mixture was allowed to cool to RT and was concentrated in vacuo to afford a brown gum which was purified by chromatography on silica, eluting with a gradient of DCM-DCM:MeOH:NH3(90: 10:1) 100-0 to 0:100. Fractions containing clean product were collected and concentrated in vacuo to afford 1-(3-chloro-5-fluoropyridin-4-yl)piperazine as a cream solid. (3.52 g, 75%). MS (ES+) 216.0.

후처리

  1. customIn a 100 mL sealed
  2. customThe vessel was sealed
  3. temperatureto cool to RT
  4. concentrationwas concentrated in vacuo
  5. customto afford a brown gum which
  6. customwas purified by chromatography on silica
  7. washeluting with a gradient of DCM-DCM
  8. additionFractions containing clean product
  9. customwere collected
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0f87d594194e4f8cabd6539a6de738c8
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340546B2

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