Pyridine → 1-benzoyl-1,4-dihydro-4-[(1-methyl-1H-benzimidazol-2-yl)methyl]pyridine

HRID 2309613Notes

Reaction equation

HRID 2309613 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH3:11].[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:12]([N:21]1[CH:26]=[CH:25][CH:24]([CH2:11][C:3]2[N:2]([CH3:1])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[N:4]=2)[CH:23]=[CH:22]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 3126931,2-Dimethylbenzimidazole

Product 1

HCID 145180941-benzoyl-1,4-dihydro-4-[(1-methyl-1H-benzimidazol-2-yl)methyl]pyridine

Procedure

To a stirred solution of 6 parts of 1,2-dimethyl-1H-benzimidazole in 50 parts of dry pyridine were added dropwise 6.2 parts of benzoyl chloride at room temperature. Upon completion, stirring was continued for 2 hours at room temperature. The whole was evaporated. The residue was dissolved in 260 parts of dichloromethane. Water was added and the solution was treated with concentrate ammonium hydroxide. The dichloromethane layer was decanted, dried, filtered and evaporated. The residue was taken up twice in 45 parts of methylbenzene and the latter was evaporated each time, yielding 1-benzoyl-1,4-dihydro-4-[(1-methyl-1H-benzimidazol-2-yl)methyl]pyridine as an oily residue (63).

Workup

  1. customThe whole was evaporated
  2. dissolutionThe residue was dissolved in 260 parts of dichloromethane
  3. additionWater was added
  4. additionthe solution was treated with concentrate ammonium hydroxide
  5. customThe dichloromethane layer was decanted
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customthe latter was evaporated each time

Sources & evidence

ORD record
ord-a4494afac54e407e882ad326f0907a87
Source dataset
uspto-grants-1987_09
Patent number
US04695575

Reaction notes

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