Potassium Iodide → N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]-ethyl}-2-pyridinecarboxamide dihydrochloride dihydrate

HRID 437672Notes

Reaction equation

HRID 437672 reaction equation
[ClH:1].[Cl:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:7].[NH:14]1[CH2:19][CH2:18][CH:17]([N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH:22][C:21]2=[O:29])[CH2:16][CH2:15]1.[I-].[K+]>CC(C)CC(=O)C>[OH2:7].[OH2:29].[ClH:2].[ClH:1].[O:29]=[C:21]1[N:20]([CH:17]2[CH2:16][CH2:15][N:14]([CH2:3][CH2:4][NH:5][C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)=[O:7])[CH2:19][CH2:18]2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[NH:22]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 21428902N-(2-chloroethyl)-2-pyridinecarboxamide hydrochloride

Product 1

HCID 21428868N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]-ethyl}-2-pyridinecarboxamide dihydrochloride dihydrate

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 2.2 parts of N-(2-chloroethyl)-2-pyridinecarboxamide hydrochloride, 6.6 parts of 1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 1.66 parts of potassium iodide and 120 parts of 4-methyl-2-pentanone is stirred and refluxed overnight. After cooling, the precipitated product is filtered off and dissolved in water. The solution is alkalized with sodium carbonate and the product is extracted three times with 4-methyl-2-pentanone. The combined extracts are washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the element is evaporated. The residue is converted into the hydrochloride salt in 2-propanone and 2-propanol. The salt is filtered off and crystallized from a mixture of ethanol and 2,2'-oxybispropane (1:1 by volume), yielding 2 parts of N-{2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]-ethyl}-2-pyridinecarboxamide dihydrochloride dihydrate; mp. 165.7° C.

Workup

  1. temperaturerefluxed overnight
  2. temperatureAfter cooling
  3. filtrationthe precipitated product is filtered off
  4. dissolutiondissolved in water
  5. extractionthe product is extracted three times with 4-methyl-2-pentanone
  6. washThe combined extracts are washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is purified by column-chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  12. customThe pure fractions are collected
  13. customthe element is evaporated
  14. filtrationThe salt is filtered off
  15. customcrystallized from a mixture of ethanol and 2,2'-oxybispropane (1:1 by volume)

Sources & evidence

ORD record
ord-847b6d49e6784c01960c29dcf6283315
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

Loading…