Water → 1-(3,4-Dimethoxy-benzyl)-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[c]azepine

HRID 458783ノート

反応式

HRID 458783 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O=P(Cl)(Cl)Cl.[BH4-].[Na+].O>C(#N)C.C(Cl)Cl.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[CH2:11][CH:12]1[C:23]2[CH:22]=[C:21]([O:24][CH3:25])[C:20]([O:26][CH3:27])=[CH:19][C:18]=2[CH2:17][CH2:16][CH2:15][NH:14]1

参加物

7

反応物 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 4311764Sodium borohydrideHCID 122679872-(3,4-Dimethoxy-phenyl)-N-[3-(3,4-dimethoxy-phenyl)-propyl]-acetamide

生成物 1

HCID 122679961-(3,4-Dimethoxy-benzyl)-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-benzo[c]azepine

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
0 °C

実験手順

A mixture of 2-(3,4-dimethoxy-phenyl)-N-[3-(3,4-dimethoxy-phenyl)-propyl]-acetamide (6.16 g, 16.49 mmol) and POCl3 (4.95 ml, 54.07 mmol) in anhydrous acetonitrile (185 ml) was stirred at reflux for 4 h under nitrogen. After cooling, the reaction mixture was concentrated in vacuo and the residue was dissolved in MeOH (125 ml). The solution was cooled to 0° C. and NaBH4 (4.31 g, 113.93 mmol) was added portionwise. After stirring at 0° C. for 2 h under nitrogen, the reaction mixture was poured into H2O and extracted three times with CH2Cl2. The combined organic extracts were washed with brine, dried over anhydrous MgSO4, filtered and concentrated to give a crude oil. Flash chromatography (CH2Cl2/MeOH: 9/1) gave the title compound as a racemic mixture (2.29 g, 6.40 mmol, 39%, yellow oil).

後処理

  1. temperatureat reflux for 4 h under nitrogen
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in MeOH (125 ml)
  5. stirringAfter stirring at 0° C. for 2 h under nitrogen
  6. extractionextracted three times with CH2Cl2
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a crude oil

出典と根拠

ORDレコード
ord-2981fe3723f64d8a8231cbac78da1c7b
出典データセット
uspto-grants-2007_03
特許番号
US07192950B2

反応ノート

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