Sodium Iodide → 1-[N-(1-Azabicyclo[3.3.0]octan-5-yl)methyl-N-ethylamino]-4-nitronaphthalene

HRID 260920ノート

反応式

HRID 260920 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1.[CH2:15]([NH:17][CH2:18][C:19]12[CH2:26][CH2:25][CH2:24][N:23]1[CH2:22][CH2:21][CH2:20]2)[CH3:16].[I-].[Na+].[OH-].[Na+]>N1C=CC=CC=1>[N:23]12[CH2:24][CH2:25][CH2:26][C:19]1([CH2:18][N:17]([C:2]1[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1)[CH2:15][CH3:16])[CH2:20][CH2:21][CH2:22]2

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 3127191-Chloro-4-nitronaphthaleneHCID 10749640N-((Hexahydro-1H-pyrrolizin-7a-yl)methyl)ethanamine

生成物 1

HCID 106170711-[N-(1-Azabicyclo[3.3.0]octan-5-yl)methyl-N-ethylamino]-4-nitronaphthalene収率 30.6%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

1-Chloro-4-nitronaphthalene (2.00 g, 9.63 mmol), 5-ethylaminomethyl-1-azabicyclo[3.3.0]octane (3.24 g, 19.3 mmol) and sodium iodide (580 mg) were added into anhydrous pyridine (20.0 ml) to react the mixture in a sealed tube for 20 hours at 190° C. After addition of aqueous sodium hydroxide solution subsequent to concentration in vacuo, the reaction mixture was extracted by ethyl acetate, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by column chromatography to afford the desired compound (1.00 g, 30.6%), as a yellow liquid.

後処理

  1. customto react the mixture in a sealed tube for 20 hours at 190° C
  2. concentrationsubsequent to concentration in vacuo
  3. extractionthe reaction mixture was extracted by ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography

出典と根拠

ORDレコード
ord-6e6833ec92c34b308874877b0333b085
出典データセット
uspto-grants-1996_06
特許番号
US05530138

反応ノート

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