Hydrochloric Acid → (E)-4-[3-(1-benzylpiperidin-4-yl)propenoyl]aniline

HRID 976125노트

반응식

HRID 976125 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[CH:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[CH:15]/[C:16]([C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=2)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 570097054-[3-(1-Benzylpiperidin-4-yl)propenoyl]nitrobenzene

생성물 1

HCID 19968908(E)-4-[3-(1-benzylpiperidin-4-yl)propenoyl]aniline

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

1.27 g of 4-[3-(1-benzylpiperidin-4-yl)propenoyl]-nitrobenzene was added to a mixed solution of 10 ml of acetic acid and 2 ml of hydrochloric acid, and then 1.38 g of stannous chloride was added thereto under ice cooling. The mixture was stirred for 24 hours while further adding 0.69 g of stannous chloride twice during the reaction. The solvent was removed under reduced pressure to obtain a crude product of (E)-4-[3-(1-benzylpiperidin-4-yl)propenoyl]aniline. Then, this was dissolved in 15 ml of ethanol, and to the solution was added 0.67 g of 4-chloro-5,6-dimethylpyrimidine. Subsequently, the mixture was reacted by heating at 60° C. for 30 minutes. The reaction mixture was neutralized by adding a 28% sodium methylate-methanol solution under cooling, solids were removed by filtration, and then the filtrate was consensed under reduced pressure. The obtained residue was applied to silica gel column chromatography to obtain 1.02 g of the title compound as pale yellow powder.

후처리

  1. customtwice during the reaction
  2. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-cbccf30b9419449380fa94a0ea80d186
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05610303

반응 노트

불러오는 중…