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

HRID 1647252ノート

反応式

HRID 1647252 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.[OH-].[Na+]>O1CCCC1>[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

5

反応物 3

HCID 4837PiperazineHCID 14798Sodium HydroxideHCID 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 79%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Add a solution of 8,11-dichloro-5,11-dihydro[1]benzothiepino[4,3-b]pyridine (8.15 g, 0.029 mol) in tetrahydrofuran (100 mL) to a stirred suspension of piperazine (28.9 g, 0.34 mol) in tetrahydrofuran (290 mL) at 18°-19° C. over 20 minutes. Stir the mixture for 4 hours at room temperature and then pour it into 2.5M aqueous NaOH (250 mL) containing ice. Separate the layers, and extract the aqueous portion with EtOAc (3×100 mL). Combine the organic portions, and wash with H2O (3×75 mL) and brine (150 mL). Dry the mixture over MgSO4, filter, and concentrate the organic layer in vacuo to obtain the crude product (8.9 g). Purify the crude product via flash chromatography (9:1:0.125 CH2Cl2 /MeOH/NH4OH) to obtain the title compound (7.6 g, 78% yield).

後処理

  1. additioncontaining ice
  2. customSeparate the layers
  3. extractionextract the aqueous portion with EtOAc (3×100 mL)
  4. washCombine the organic portions, and wash with H2O (3×75 mL) and brine (150 mL)
  5. dry with materialDry the mixture over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate the organic layer in vacuo
  8. customto obtain the crude product (8.9 g)
  9. customPurify the crude product via flash chromatography (9:1:0.125 CH2Cl2 /MeOH/NH4OH)

出典と根拠

ORDレコード
ord-7b179e8ebc574687b8530206fafb0149
出典データセット
uspto-grants-1995_07
特許番号
US05430032

反応ノート

読み込み中…