Pyridine → N-(2-Pyridinylmethyl)-4-(tetradecyloxy)benzamide

HRID 247914

反応式

HRID 247914 の反応式
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.N1C=CC=CC=1.[CH2:15]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>C(Cl)Cl>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][NH:1][C:34](=[O:35])[C:33]1[CH:32]=[CH:31][C:30]([O:29][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:38][CH:37]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 195092-PyridinemethanamineHCID 9998158Benzoyl chloride, 4-(tetradecyloxy)-

生成物 1

HCID 10093859N-(2-Pyridinylmethyl)-4-(tetradecyloxy)benzamide収率 62.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a 0° C. solution of 0.674 g 2-(aminomethyl)pyridine, 20 ml methylene chloride and 1.83 ml pyridine is added, dropwise over 20 minutes, 2.0 g of product from Example 3 dissolved in 25 ml of methylene chloride. The reaction is stirred at 0° C. for 2 hours followed by stirring at room temperature for 17 hours. The reaction mixture is partitioned between chloroform and saturated sodium bicarbonate, washed with water and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:75% ethyl acetate/hexane) to give 1.51 g of the desired product.

後処理

  1. stirringby stirring at room temperature for 17 hours
  2. customThe reaction mixture is partitioned between chloroform and saturated sodium bicarbonate
  3. washwashed with water and saturated sodium chloride
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by column chromatography (silica gel:75% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-0e0c972d4a26450c9db43ea2b4fff5c1
出典データセット
uspto-grants-1993_05
特許番号
US05208247

関連ノート

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