1,3-dihydro-1-methyl-3-(3-pyridinylmethyl)-2H-benzimidazol-2-one → 1,3-dihydro-1-methyl-3-(3-piperidinylmethyl)-2H-benzimidazol-2-one

HRID 2051687Notes

Reaction equation

HRID 2051687 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[C:3]1=[O:18].[H][H]>[Pd].C(O)(=O)C>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]2)[C:3]1=[O:18]

Participants

5

Reactant 2

HCID 203795071,3-dihydro-1-methyl-3-(3-pyridinylmethyl)-2H-benzimidazol-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 203794921,3-dihydro-1-methyl-3-(3-piperidinylmethyl)-2H-benzimidazol-2-oneYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 16 parts of 1,3-dihydro-1-methyl-3-(3-pyridinylmethyl)-2H-benzimidazol-2-one and 200 parts of acetic acid is hydrogenated at normal pressure and at 50° C. with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. Water is added to the residue and the whole is alkalized with ammonium hydroxide. The product is extracted with methylbenzene. The extract is dried, filtered and evaporated, yielding 16.5 parts (100%) of 1,3-dihydro-1-methyl-3-(3-piperidinylmethyl)-2H-benzimidazol-2-one as an oily residue.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. additionWater is added to the residue
  4. extractionThe product is extracted with methylbenzene
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-6de8c339633b485ebd52f7807a8bf614
Source dataset
uspto-grants-1980_01
Patent number
US04181802

Reaction notes

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