Pyridine → N-[2-(2-Pyridinyl)ethyl]-4-(tetradecyloxy)benzamide

HRID 247967

반응식

HRID 247967 반응식
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.N1C=CC=CC=1.[CH2:16]([O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(Cl)Cl.C(Cl)(Cl)Cl>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][CH2:2][NH:1][C:35](=[O:36])[C:34]1[CH:33]=[CH:32][C:31]([O:30][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:39][CH:38]=1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 759192-PyridineethanamineHCID 9998158Benzoyl chloride, 4-(tetradecyloxy)-

생성물 1

HCID 10478314N-[2-(2-Pyridinyl)ethyl]-4-(tetradecyloxy)benzamide수율 41.2%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To a 0° solution of 2.54 g of 2-(2-aminoethyl)pyridine, 50 ml of methylene chloride and 6.42 ml of pyridine is added, dropwise, 7.0 g of product from Example 3 in 250 ml of methylene chloride. The reaction is stirred at 0° C. for 2 hours followed by 14 hours at room temperature. The reaction is diluted with chloroform, washed with saturated sodium bicarbonate, water and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:75-100% ethyl acetate/hexane) to give 3.58 g of the desired product.

후처리

  1. waitfollowed by 14 hours at room temperature
  2. washwashed with saturated sodium bicarbonate, water and saturated sodium chloride
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography (silica gel:75-100% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-3d766805a00346a79f60fb0a4ee3c4ec
출처 데이터셋
uspto-grants-1993_05
특허 번호
US05208247

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