Hydrazine hydrate (1:1) → Benzenepentanamine

HRID 1486558ノート

反応式

HRID 1486558 の反応式
O.NN.[C:4]1([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]2C(=O)C3C(=CC=CC=3)C2=O)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CCO>[C:4]1([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 6261932-(5-Phenylpentyl)isoindoline-1,3-dione

生成物 1

HCID 140275Benzenepentanamine収率 74.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Hydrazine monohydrate (0.36 g, 7.2 mmol) was added to a solution of 2-(5-phenylpentyl)isoindoline-1,3-dione (0.68 g, 2.3 mmol) in 25 mL of EtOH. The solution was stirred under reflux for 5 hrs and then cooled to room temperature. The white precipitate was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in a 1N solution of NaOH (80 mL) and extracted with chloroform (3×70 mL). The combined organic layers were washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The crude was purified by column chromatography using a Teledyne ISCO apparatus (solid deposition with TEA, eluent: 20% MeOH in dichloromethane with 1% of TEA) to afford the title compound (0.28 g, 73%) as a white solid. 1H NMR (400 MHz, CDCl3): 1.37-1.48 (m, 2H), 1.58-1.72 (m, 4H), 2.57-2.69 (m, 2H), 3.29 (t, J=6.70 Hz, 2H), 7.13-7.24 (m, 3H), 7.26-7.34 (m, 2H).

後処理

  1. temperatureunder reflux for 5 hrs
  2. customThe white precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in a 1N solution of NaOH (80 mL)
  5. extractionextracted with chloroform (3×70 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. customthe solvent was removed under reduced pressure
  9. customThe crude was purified by column chromatography

出典と根拠

ORDレコード
ord-68be55fa81024c86b66ce29e7064df47
出典データセット
uspto-grants-2016_08
特許番号
US09428465B2

反応ノート

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