Acetic Acid → 1-(4-fluorophenylmethyl)-N-[1-[2-(2-pyrazinyl)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine

HRID 620509Notes

Reaction equation

HRID 620509 reaction equation
[CH:1]([C:3]1[CH:8]=[N: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)(=O)C>CO>[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]=[N:7][CH:6]=[CH:5][N:4]=3)[CH2:31][CH2:32]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 77840VinylpyrazineHCID 123618Tecastemizole

Product 1

HCID 135881191-(4-fluorophenylmethyl)-N-[1-[2-(2-pyrazinyl)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.27 parts of 2-ethenylpyrazine, 6.48 parts of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amine, 0.3 parts of acetic acid and 40 parts of methanol was stirred and refluxed for 48 hours. The solvent was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (88:12 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was washed with 2,2'-oxybispropane and crystallized from 27 parts of methylbenzene, yielding 2.4 parts of 1-(4-fluorophenylmethyl)-N-[1-[2-(2-pyrazinyl)ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 165.3° C. (compound 101).

Workup

  1. temperaturerefluxed for 48 hours
  2. customThe solvent was evaporated
  3. customThe residue was purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (88:12 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. washThe residue was washed with 2,2'-oxybispropane
  8. customcrystallized from 27 parts of methylbenzene

Sources & evidence

ORD record
ord-0e47ac838e824bde93b4b5796cc5997f
Source dataset
uspto-grants-1989_04
Patent number
US04820822

Reaction notes

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