2-Vinylpyridine → 1-[(4-Fluorophenyl)methyl]-N-{1-[2-(pyridin-2-yl)ethyl]piperidin-4-yl}-1H-benzimidazol-2-amine

HRID 1856561Notes

Reaction equation

HRID 1856561 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)=[CH2:2].[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=[C:18]2[NH:26][CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:12][CH:11]=1>C(O)CCC>[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=[C:18]2[NH:26][CH:27]2[CH2:28][CH2:29][N:30]([CH2:2][CH2:1][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=3)[CH2:31][CH2:32]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 75212-VinylpyridineHCID 123618Tecastemizole

Product 1

HCID 102520561-[(4-Fluorophenyl)methyl]-N-{1-[2-(pyridin-2-yl)ethyl]piperidin-4-yl}-1H-benzimidazol-2-amineYield 23%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2.1 parts of 2-(ethenyl)pyridine, 3.25 parts of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amine and 80 parts of 1-butanol is stirred and refluxed overnight. The reaction mixture is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2,2'-oxybispropane, yielding 1 part (23%) of 1-[(4-fluorophenyl)methyl]-N-{1-[2-(2-pyridinyl)ethyl]-4-piperidinyl}-1H-benzimidazol-2-amine; mp. 133.4° C.

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture is evaporated
  3. customThe residue is purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated
  7. customThe residue is crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-3e33f447054f44c89b8837700da7c7cf
Source dataset
uspto-grants-1980_08
Patent number
US04219559

Reaction notes

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