Pyrrolidine → 8-Bromo-3-pyrrolidino-1,2-dihydronaphthalene

HRID 233806ノート

反応式

HRID 233806 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][C:9](=O)[CH2:8][CH2:7]2.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH2:9][C:8]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[CH:7]2

参加物

4

反応物 2

HCID 31268PyrrolidineHCID 41361878-Bromo-1,2,3,4-tetrahydronaphthalen-2-one

生成物 1

HCID 190432148-Bromo-3-pyrrolidino-1,2-dihydronaphthalene

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 8-bromo-2-tetralone (10 gm, 44.4 mMol) in toluene (175 ml) was added pyrrolidine (6.6 ml), and the solution was stirred at reflux for three hours. The volatiles were removed in vacuo to give 8-bromo-3-pyrrolidino-1,2-dihydronaphthalene as a brown oil. To this oil in p-dioxane (60 mL) was added methyl iodide (20 mL, 322 mMol), and the resulting solution was stirred at reflux for eighteen hours. The reaction mixture was diluted with water (60 mL) and acetic acid (3.2 mL), and heating was continued for an additonal three hours. After this time the solution was cooled to room temperature and the volatiles removed in vacuo. The residue was suspended in water and extracted well with diethyl ether. The organic phases were combined, washed with saturated aqueous NaHCO3, dried with Na2SO4 and concentrated in vacuo to give an orange oil. Purification by flash chromatography (33% diethyl ether in hexane) gave the title compound as a light orange oil (6.88 gm, 65%).

後処理

  1. temperatureat reflux for three hours
  2. customThe volatiles were removed in vacuo

出典と根拠

ORDレコード
ord-cd7f7891591d4e3492ca2202878202e0
出典データセット
uspto-grants-1997_01
特許番号
US05594025

反応ノート

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