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

HRID 323193

反応式

HRID 323193 の反応式
[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

参加物

3

反応物 1

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

生成物 1

HCID 123618Tecastemizole

試薬・触媒・溶媒 1

HCID 260Hydrogen Bromide溶媒

実験手順

Combine (1-(4-fluorobenzyl)-1H-benzimidazol-2-yl)-(1-ethoxycarbonyl-piperidin-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.

後処理

  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

出典と根拠

ORDレコード
ord-80d71fb58aea40af941dbd037c6b7708
出典データセット
uspto-grants-2001_04
特許番号
US06211199B1

関連ノート

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