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

HRID 247914

반응식

HRID 247914 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0e0c972d4a26450c9db43ea2b4fff5c1
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05208247

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