Ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-YL]amino]piperidine-1-carboxylate → Tecastemizole

HRID 582060

반응식

HRID 582060 반응식
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[NH:16][CH:17]2[CH2:22][CH2:21][N:20](C(OCC)=O)[CH2:19][CH2:18]2)=[CH:4][CH:3]=1>Br>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[NH:16][CH:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)=[CH:28][CH:29]=1

참가 물질

3

반응물 1

HCID 3019916Ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-YL]amino]piperidine-1-carboxylate

생성물 1

HCID 123618Tecastemizole

시약·촉매·용매 1

HCID 260Hydrogen Bromide용매

실험 절차

Combine (1-(4-fluorobenzyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine (31.5 g, 79.4 mmol) and 48% hydrobromic acid (250 mL). Heat to reflux. After 1.5 hours, cool and evaporate in vacuo to give a residue. Add water and sodium hydroxide (60 g) and extract with chloroform. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a solid. Collect the solid by filtration and recrystallize from hexane/chloroform to give, after drying, the title compound: mp; 212-215° C.

후처리

  1. temperatureHeat to reflux
  2. temperaturecool
  3. customevaporate in vacuo
  4. customto give a residue
  5. extractionAdd water and sodium hydroxide (60 g) and extract with chloroform
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customto obtain a solid
  10. customCollect the solid
  11. filtrationby filtration
  12. customrecrystallize from hexane/chloroform
  13. customto give
  14. customafter drying

출처 및 근거

ORD 기록
ord-bb18db8f46154753b8c4874bc149b77f
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05922737

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