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

HRID 524873ノート

反応式

HRID 524873 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0f87d594194e4f8cabd6539a6de738c8
出典データセット
uspto-grants-2016_05
特許番号
US09340546B2

反応ノート

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