Piperazine → 8-Chloro-5,11-dihydro-11-(1-piperazinyl)[1]benzothiepino[4,3-b]pyridine

HRID 366777ノート

反応式

HRID 366777 の反応式
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[CH:6](Cl)[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C1COCC1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[CH:6]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3

参加物

4

反応物 2

HCID 4837PiperazineHCID 15280235HCID 15280235、化合物

生成物 1

HCID 157805018-Chloro-5,11-dihydro-11-(1-piperazinyl)[1]benzothiepino[4,3-b]pyridine収率 91.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A slurry of 8,11-dichloro-5,11-dihydro-[1]benzothiepino[4,3-b]pyridine (3.79 g, 13.43 mmol) in THF (25 ml) was added dropwise to piperazine (3.53 g, 157 mmol) in THF (50 ml) over 45 minutes. The mixture was stirred at room temperature for 5 hours and the reaction was then quenched with the slow addition of NaOH (200 ml, 2.5N) and extracted with CH2Cl2 (400 ml and 4×100 ml). The combined organic layers were washed with brine, dried (Na2SO4), decanted and concentrated; the crude product was purified by flash chromatography (10%acetone/CH2Cl2 to 10%MeOH/CH2Cl2 /NH4OH) and obtained as a white solid (4.08 g, 91%); MS (FAB, M+H)=332; found: C, 61.73; H, .5.60; N, 12.40; C17H18ClN3S requires: C, 61.53; H, 5.47; N, 12.66.

後処理

  1. customthe reaction was then quenched with the slow addition of NaOH (200 ml, 2.5N)
  2. extractionextracted with CH2Cl2 (400 ml and 4×100 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customdecanted
  6. concentrationconcentrated
  7. customthe crude product was purified by flash chromatography (10%acetone/CH2Cl2 to 10%MeOH/CH2Cl2 /NH4OH)

出典と根拠

ORDレコード
ord-bcd5fc92bfd94b62be628d35ece752a4
出典データセット
uspto-grants-2000_10
特許番号
US06130229

反応ノート

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