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Methyl iodide → 2-[2-(4-Pyridyl)ethylamino]acetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

HRID 11480
ノート
印刷プレビュー

反応式

HRID 11480 の反応式
[C:1]12([CH2:11][CH2:12][N:13]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:14](=[O:17])[CH2:15]Br)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(=O)([O-])[O-].[K+].[K+].CI.[NH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1>CN(C)C=O.C(OCC)C.O>[C:1]12([CH2:11][CH2:12][N:13]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:14](=[O:17])[CH2:15][NH:31][CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 832754-PyridineethanamineHCID 574798992-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

生成物 1

HCID 574798982-[2-(4-Pyridyl)ethylamino]acetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide収率 41.6%

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 3283Diethyl Ether溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

Next, 2-bromoacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide (1.3 g, 3.5 mmol) was dissolved in anhydrous N,N-dimethylformamide (30 ml), potassium carbonate (1.5 g, 11 mmol), methyl iodide (1.6 g, 11 mmol) and 4-(2-aminoethyl)pyridine (0.43 g, 3.5 mmol) were added to the solution, and the mixture was stirred at an external temperature of 75° C. overnight. Water (100 ml) and diethyl ether (100 ml) were added to the reaction mixture, the reaction mixture was distributed, and the diethyl ether layer was washed with water (70 ml) twice and a saturated aqueous sodium chloride solution (120 ml) once successively and dried over anhydrous magnesium sulfate. The diethyl ether layer was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography to give 0.6 g (40%) of the titled compound as an oily matter.

後処理

  1. washthe diethyl ether layer was washed with water (70 ml) twice
  2. dry with materiala saturated aqueous sodium chloride solution (120 ml) once successively and dried over anhydrous magnesium sulfate
  3. concentrationThe diethyl ether layer was concentrated under reduced pressure
  4. customthe concentrate was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-9c3e5bf933da48958d386228a5bce4fa
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07098226B2

反応ノート

読み込み中…

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