Hydrochloric Acid → 1-(1-Benzyl-3-methoxymethylpyrrolidin-3-yl)methylamine

HRID 10352ノート

反応式

HRID 10352 の反応式
O.NN.[CH2:4]([N:11]1[CH2:15][CH2:14][C:13]([CH2:19][N:20]2C(=O)C3C(=CC=CC=3)C2=O)([CH2:16][O:17][CH3:18])[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl>C(O)C>[CH2:4]([N:11]1[CH2:15][CH2:14][C:13]([CH2:19][NH2:20])([CH2:16][O:17][CH3:18])[CH2:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 578326372-(1-Benzyl-3-methoxymethylpyrrolidin-3-ylmethyl)isoindole-1,3-dione

生成物 1

HCID 219789711-(1-Benzyl-3-methoxymethylpyrrolidin-3-yl)methylamine収率 89.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Hydrazine hydrate (85% solution in water, 0.372 g, 6.32 mmol) is added to a solution of 2-(1-benzyl-3-methoxymethylpyrrolidin-3-ylmethyl)isoindole-1,3-dione (Example A20, 1.581 g, 4.34 mmol) in ethanol (50 mL). The resulting mixture is refluxed for 4.5 hours, cooled and acidified with concentrated hydrochloric acid. The precipitate is removed by filtration and the filtrate is concentrated in vacuo. The residue is dissolved in ethanol/water (2:1) and the insoluble material is removed by filtration. The filtrate is basified to pH 10 with 1N sodium hydroxide solution and extracted with dichloromethane. The combined organic extracts are dried over Na2SO4, filtered and concentrated under vacuum to afford the title compound (0.910 g). 1H NMR (200 MHz, CDCl3): δ 7.41–7.15 (m, 5H), 3.57 (s, 2H), 3.33 (s, 3H), 3.30 (s, 2H), 2.71 (s, 2H), 2.64–2.51 (m, 2H), 2.42–2.24 (m, 2H), 1.68–1.52 (m, 2H), 1.38–1.10 (m, 2H).

後処理

  1. temperatureThe resulting mixture is refluxed for 4.5 hours
  2. temperaturecooled
  3. customThe precipitate is removed by filtration
  4. concentrationthe filtrate is concentrated in vacuo
  5. dissolutionThe residue is dissolved in ethanol/water (2:1)
  6. customthe insoluble material is removed by filtration
  7. extractionextracted with dichloromethane
  8. dry with materialThe combined organic extracts are dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-bb473ca2021b44e6ad238522ab891e1c
出典データセット
uspto-grants-2006_08
特許番号
US07094780B1

反応ノート

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