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

HRID 323193

Reaction equation

HRID 323193 reaction equation
[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

Participants

3

Reactant 1

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

Product 1

HCID 123618Tecastemizole

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-80d71fb58aea40af941dbd037c6b7708
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Linked notes

Loading…