Hydrochloric Acid → 2-{6-Methoxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzaldehyde

HRID 916856ノート

反応式

HRID 916856 の反応式
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[S:16][C:15]2[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:14]=2[C:13]=1[C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[CH:27][CH:26]=1)=[O:24].Cl.O>C1COCC1.C(Cl)Cl>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:14]2[C:13]([C:23](=[O:24])[C:25]3[CH:26]=[CH:27][C:28]([O:31][CH2:32][CH2:33][N:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)=[CH:29][CH:30]=3)=[C:12]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[CH:2]=[O:1])[S:16][C:15]=2[CH:17]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 17987059[2-(2-[1,3]Dioxolan-2-yl-phenyl)-6-methoxy-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

生成物 1

HCID 179870572-{6-Methoxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzaldehyde

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of [2-(2-[1,3]dioxolan-2-yl-phenyl)-6-methoxy-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (crude) in THF (15 mL), add HCl (2 mL, 5M) and water (2 mL). Heat the mixture to reflux for 30 min. Dilute with CH2Cl2 and quench with aq. NaHCO3. Wash the organic phase with water and brine, dry over MgSO4, filter and concentrate. Purify the crude product by flash chromatography (0-10% (2M NH3 in MeOH)/CH2Cl2) to afford 2-{6-methoxy-3-[4(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzaldehyde (410 mg) which is contaminated with unidentified byproducts and is used without further purification.

後処理

  1. temperatureHeat the mixture
  2. temperatureto reflux for 30 min
  3. customquench with aq. NaHCO3
  4. washWash the organic phase with water and brine
  5. dry with materialdry over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the crude product by flash chromatography (0-10% (2M NH3 in MeOH)/CH2Cl2)

出典と根拠

ORDレコード
ord-22293cc7e9604755ab8c0c19252e6728
出典データセット
uspto-grants-2007_09
特許番号
US07271264B2

反応ノート

読み込み中…